SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 13, 2008, Pages 1961-1964

Synthesis of novel 3-oxopiperidin-2-ones from methyl 2-alkoxy-5-amino-2- pentenoates

(3) Dejaegher, Yves a D'Hooghe, Matthias a De Kimpe, Norbert a

a GHENT UNIVERSITY (Belgium)

Author keywords

3 Oxopiperidin 2 ones; Acid hydrolysis; Azetidin 2 ones; Ring closure; Lactams

Indexed keywords

3 OXOPIPERIDIN 2 ONE DERIVATIVE; 4 (1 CHLORO 1 METHYLETHYL)AZETIDINE 2 ONE DERIVATIVE; 4 (2 HALO 1,1 DIMETHYLETHYL)AZETIDIN 2 ONE DERIVATIVE; AZETIDINE DERIVATIVE; METHANOL; METHOXIDE SODIUM; METHYL 2 ALKOXY 5 AMINO 2 PENTENOATE DERIVATIVE; OXIDE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFURIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 49649109612 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077970 Document Type: Article

Times cited : (8)

References (54)

1
- 0343522919
- (a) Page, M. I. Ace. Chem. Res. 1984, 17, 144.
- (1984) Ace. Chem. Res , vol.17 , pp. 144
- Page, M.I.¹

2
- 0001596755
- (b) Page, M. I. Adv. Phys. Org. Chem. 1987, 23, 165.
- (1987) Adv. Phys. Org. Chem , vol.23 , pp. 165
- Page, M.I.¹

3
- 0034725847
- (c) Page, M. L; Laws, A. P. Tetrahedron 2000, 56, 5631.
- (2000) Tetrahedron , vol.56 , pp. 5631
- Page, M.L.¹ Laws, A.P.²

4
- 0004015248
- Georg, G. L, Ed, Wiley: New York
- (d) The Organic Chemistry of β-Lactams; Georg, G. L, Ed.; Wiley: New York, 1993.
- (1993) The Organic Chemistry of β-Lactams

5
- 80054090549
- Azetidines, Azetines, and Azetes: Monocyclic
- Katritzky, A, Ramsden, C, Scriven, E, Taylor, R, Eds, Elsevier: Oxford
- (e) Singh, G. S.; D'hooghe, M.; De Kimpe, N. Azetidines, Azetines, and Azetes: Monocyclic, In Comprehensive Heterocyclic Chemistry III, A Review of the Literature 1995-2007, Vol. 2; Katritzky, A.; Ramsden, C.; Scriven, E.; Taylor, R., Eds.; Elsevier: Oxford, 2008, 1-110.
- (2008) Comprehensive Heterocyclic Chemistry III, A Review of the Literature 1995-2007 , vol.2 , pp. 1-110
- Singh, G.S.¹ D'hooghe, M.² De Kimpe, N.³

6
- 0004030275
- Page, M. I, Ed, Chapman and Hall: London
- (f) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.
- (1992) The Chemistry of β-Lactams

7
- 33845183324
- (g) Hart, D. J.; Ha, D. C. Chem. Rev. 1989, 89, 1447.
- (1989) Chem. Rev , vol.89 , pp. 1447
- Hart, D.J.¹ Ha, D.C.²

8
- 0000096261
- (a) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
- (1995) Acc. Chem. Res , vol.28 , pp. 383
- Ojima, I.¹

9
- 0000727123
- (b) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 377.
- (1997) Chem. Soc. Rev , pp. 377
- Ojima, I.¹ Delaloge, F.²

10
- 0041760054
- (c) Singh, G. S. Tetrahedron 2003, 59, 7631.
- (2003) Tetrahedron , vol.59 , pp. 7631
- Singh, G.S.¹

11
- 4143125756
- (d) France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
- (2004) Acc. Chem. Res , vol.37 , pp. 592
- France, S.¹ Weatherwax, A.² Taggi, A.E.³ Lectka, T.⁴

12
- 14844362964
- (e) Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Chem. Rev. 2005, 105, 395.
- (2005) Chem. Rev , vol.105 , pp. 395
- Fisher, J.F.¹ Meroueh, S.O.² Mobashery, S.³

13
- 36849034419
- (f) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
- (2007) Chem. Rev , vol.107 , pp. 4437
- Alcaide, B.¹ Almendros, P.² Aragoncillo, C.³

14
- 0035858673
- (a) Lee, H. K.; Chun, J. S.; Pak, C. S. Tetrahedron Lett. 2001, 42, 3483.
- (2001) Tetrahedron Lett , vol.42 , pp. 3483
- Lee, H.K.¹ Chun, J.S.² Pak, C.S.³

15
- 0037459751
- (b) Lee, H. K.; Chun, J. S.; Pak, C. S. J. Org. Chem. 2003, 68, 2471.
- (2003) J. Org. Chem , vol.68 , pp. 2471
- Lee, H.K.¹ Chun, J.S.² Pak, C.S.³

16
- 0041743187
- (c) Lee, H. K.; Chun, J. S.; Pak, C. S. Tetrahedron 2003, 59, 6445.
- (2003) Tetrahedron , vol.59 , pp. 6445
- Lee, H.K.¹ Chun, J.S.² Pak, C.S.³

17
- 24944457136
- (d) Kvrno, L.; Werder, M.; Hauser, H.; Carreira, E. M. J. Med. Chem. 2005, 48, 6035.
- (2005) J. Med. Chem , vol.48 , pp. 6035
- Kvrno, L.¹ Werder, M.² Hauser, H.³ Carreira, E.M.⁴

18
- 33644650296
- (e) Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 2159.
- (2006) J. Org. Chem , vol.71 , pp. 2159
- Huguenot, F.¹ Brigaud, T.²

19
- 33344478127
- (f) Del Buttero, P.; Molteni, G.; Roncoroni, M. Tetrahedron Lett. 2006, 47, 2209.
- (2006) Tetrahedron Lett , vol.47 , pp. 2209
- Del Buttero, P.¹ Molteni, G.² Roncoroni, M.³

20
- 33847794079
- (g) Mishra, R. K.; Coates, C. M.; Revell, K. D.; Turos, E. Org. Lett. 2007, 9, 575.
- (2007) Org. Lett , vol.9 , pp. 575
- Mishra, R.K.¹ Coates, C.M.² Revell, K.D.³ Turos, E.⁴

21
- 35348912513
- (h) Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. J. Org. Chem. 2007, 72, 7980.
- (2007) J. Org. Chem , vol.72 , pp. 7980
- Alcaide, B.¹ Almendros, P.² Cabrero, G.³ Ruiz, M.P.⁴

22
- 41149095109
- (i) D'hooghe, M.; Dekeukeleire, S.; De Kimpe, N. Org. Biomol. Chem. 2008, 6, 1190.
- (2008) Org. Biomol. Chem , vol.6 , pp. 1190
- D'hooghe, M.¹ Dekeukeleire, S.² De Kimpe, N.³

23
- 1442324529
- (a) Otaka, A.; Watanabe, J.; Yukimasa, A.; Sasaki, Y.; Watanabe, H.; Kinoshita, T.; Oishi, S.; Tamamura, H.; Fujii, N. J. Org. Chem. 2004, 69, 1634.
- (2004) J. Org. Chem , vol.69 , pp. 1634
- Otaka, A.¹ Watanabe, J.² Yukimasa, A.³ Sasaki, Y.⁴ Watanabe, H.⁵ Kinoshita, T.⁶ Oishi, S.⁷ Tamamura, H.⁸ Fujii, N.⁹

24
- 5344243182
- (b) Kvaerno, L.; Ritter, T.; Werder, M.; Hauser, H.; Carreira, E. M. Angew. Chem. Int. Ed. 2004, 43, 4653.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 4653
- Kvaerno, L.¹ Ritter, T.² Werder, M.³ Hauser, H.⁴ Carreira, E.M.⁵

25
- 7044269424
- (c) Dondoni, A.; Massi, A.; Sabbatini, S.; Bertolasi, V. Adv. Synth. Catal. 2004, 346, 1355.
- (2004) Adv. Synth. Catal , vol.346 , pp. 1355
- Dondoni, A.¹ Massi, A.² Sabbatini, S.³ Bertolasi, V.⁴

26
- 10844281934
- (d) Battaglia, A.; Guerrini, A.; Bertucci, C. J. Org. Chem. 2004, 69, 9055.
- (2004) J. Org. Chem , vol.69 , pp. 9055
- Battaglia, A.¹ Guerrini, A.² Bertucci, C.³

27
- 27144471913
- (e) Ritter, T.; Kvaerno, L.; Werder, M.; Hauser, H.; Carreira, E. M. Org. Biomol. Chem. 2005, 3, 3514.
- (2005) Org. Biomol. Chem , vol.3 , pp. 3514
- Ritter, T.¹ Kvaerno, L.² Werder, M.³ Hauser, H.⁴ Carreira, E.M.⁵

28
- 30944444606
- (f) Boros, E.; Bertha, F.; Czira, G.; Feller, A.; Fetter, J.; Kajtar-Peredy, M.; Simig, G. J. Heterocycl. Chem. 2006, 43, 87.
- (2006) J. Heterocycl. Chem , vol.43 , pp. 87
- Boros, E.¹ Bertha, F.² Czira, G.³ Feller, A.⁴ Fetter, J.⁵ Kajtar-Peredy, M.⁶ Simig, G.⁷

29
- 33846423142
- (g) De Vitis, L.; Troisi, L.; Granito, C.; Pindinelli, E.; Ronzini, L. Eur. J. Org. Chem. 2007, 356.
- (2007) Eur. J. Org. Chem , pp. 356
- De Vitis, L.¹ Troisi, L.² Granito, C.³ Pindinelli, E.⁴ Ronzini, L.⁵

30
- 0035855293
- (a) Abbiati, G.; Rossi, E. Tetrahedron 2001, 57, 7205.
- (2001) Tetrahedron , vol.57 , pp. 7205
- Abbiati, G.¹ Rossi, E.²

31
- 0037427991
- (b) Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 35.
- (2003) J. Org. Chem , vol.68 , pp. 35
- Durham, T.B.¹ Miller, M.J.²

32
- 0037697025
- (c) Hafez, A. M.; Dudding, T.; Wagerle, T. R.; Shah, M. H.; Taggi, A. E.; Lectka, T. J. Org. Chem. 2003, 68, 5819.
- (2003) J. Org. Chem , vol.68 , pp. 5819
- Hafez, A.M.¹ Dudding, T.² Wagerle, T.R.³ Shah, M.H.⁴ Taggi, A.E.⁵ Lectka, T.⁶

33
- 0038305124
- (d) Gerona-Navarro, G.; Garcia-Lopez, M. T.; Gonzalez-Muniz, R. Tetrahedron Lett. 2003, 44, 6145.
- (2003) Tetrahedron Lett , vol.44 , pp. 6145
- Gerona-Navarro, G.¹ Garcia-Lopez, M.T.² Gonzalez-Muniz, R.³

34
- 3943057458
- (e) Basak, A.; Ghosh, S. C. Synlett 2004, 1637.
- (2004) Synlett , pp. 1637
- Basak, A.¹ Ghosh, S.C.²

35
- 31544475942
- (f) Li, X.-G.; Kanerva, L. T. Adv. Synth. Catal. 2006, 348, 197.
- (2006) Adv. Synth. Catal , vol.348 , pp. 197
- Li, X.-G.¹ Kanerva, L.T.²

36
- 0033525476
- Khim, S.-K.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1827.
- (1999) Tetrahedron Lett , vol.40 , pp. 1827
- Khim, S.-K.¹ Nuss, J.M.²

37
- 4344678639
- Dejaegher, Y.; De Kimpe, N. J. Org. Chem. 2004, 69, 5974.
- (2004) J. Org. Chem , vol.69 , pp. 5974
- Dejaegher, Y.¹ De Kimpe, N.²

38
- 49649090479
- Representative Procedure; Synthesis of 1-Isopropyl-5,5- dimethylpiperidine-2,3-dione (6c, To (Z)-methyl 5-isopropylamino-2-methoxy- 4,4-dimethyl-2-pentenoate(4c; 0.50 g, 2.2 mmol)7 was added coned sulfuric acid (0.6 mL, 21.6 mmol) dropwise. The resulting homogeneous mixture was stirred at r.t. for 1 h and subsequently cooled to O °C. NaOH (1 M) was added cautiously dropwise until pH 10, the resulting aqueous phase was extracted with CH2Cl2 (3x5 mL) and the combined organic phases were dried (MgSO4, After filtration and evaporation of the solvent, crude 5,5-dimethyl-l-isopropylpiperidine-2,3-dione (6c) was purified by filtration over silica gel using EtOAc. 1-Isopropyl-5,5-dimethylpiperidine-2, 3-dione (6c, yield: 50, 1H NMR (270 MHz, CDCl3, δ, 1.13 (s, 6 H, CqMe2, 1.18 (d, J= 6.6 Hz, 6 H, CHCe2, 2.54 [s, 2 H, C(O)CH2, 3.22 s, 2 H
- 2: C, 65.54; H, 9.35; N, 7.64. Found: C, 65.43; H, 9.51; N, 7.53.

39
- 0033775563
- (a) O'Hagan, D. Nat. Prod. Rep. 2000,17, 435.
- (2000) Nat. Prod. Rep , vol.17 , pp. 435
- O'Hagan, D.¹

40
- 0037459890
- (b) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953.
- (2003) Tetrahedron , vol.59 , pp. 2953
- Weintraub, P.M.¹ Sabol, J.S.² Kane, J.M.³ Borcherding, D.R.⁴

41
- 0842268019
- (c) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
- (2004) Tetrahedron , vol.60 , pp. 1701
- Buffat, M.G.P.¹

42
- 0026030568
- (a) Schreiber, S. L. Science 1991, 251, 283.
- (1991) Science , vol.251 , pp. 283
- Schreiber, S.L.¹

43
- 0033868126
- (b) Kahn, K.; Bruice, T. C. Bioorg. Med. Chem. 2000, 8, 1881.
- (2000) Bioorg. Med. Chem , vol.8 , pp. 1881
- Kahn, K.¹ Bruice, T.C.²

44
- 0022632343
- (a) Lounasmaa, M.; Somersalo, P. Tetrahedron 1986, 42, 1501.
- (1986) Tetrahedron , vol.42 , pp. 1501
- Lounasmaa, M.¹ Somersalo, P.²

45
- 0033978533
- (b) Jung, A.; Koch, O.; Ries, M.; Schaumann, E. Synlett 2000, 92.
- (2000) Synlett , pp. 92
- Jung, A.¹ Koch, O.² Ries, M.³ Schaumann, E.⁴

46
- 0345435969
- (c) Forns, P.; Fernández, M. M.; Diez, A.; Rubiralta, M.; Cherrier, M. P.; Bonin, M.; Quirion, J.-C. Synthesis 1999, 258.
- (1999) Synthesis , pp. 258
- Forns, P.¹ Fernández, M.M.² Diez, A.³ Rubiralta, M.⁴ Cherrier, M.P.⁵ Bonin, M.⁶ Quirion, J.-C.⁷

47
- 49649095269
- Herdeis, C.; Bissinger, G. Z. Naturforsch., B 1987, 42, 785.
- (1987) Z. Naturforsch., B , vol.42 , pp. 785
- Herdeis, C.¹ Bissinger, G.²

48
- 0001342325
- (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573.
- (1985) J. Org. Chem , vol.50 , pp. 3573
- Wasserman, H.H.¹ Ives, J.L.²

49
- 0019254820
- (b) Edelstein, F.; Avramoff, M.; Shtacher, G.; Teitz, Y. Eur. J. Med. Chem. 1980, 15, 566.
- (1980) Eur. J. Med. Chem , vol.15 , pp. 566
- Edelstein, F.¹ Avramoff, M.² Shtacher, G.³ Teitz, Y.⁴

50
- 33745123026
- (c) Pinto, D. J. P.; Orwat, M. J.; Quan, M. L.; Han, Q.; Galemmo, R. A.; Amparo, E.; Wells, B.; Ellis, C.; He, M. Y.; Alexander, R. S.; Rossi, K. A.; Smallwood, A.; Wong, P. C.; Luettgen, J. M.; Rendina, A. R.; Knabb, R. M.; Mersinger, L.; Kettner, C.; Bai, S.; He, K.; Wexler, R. R.; Lam, P. Y. S. Bioorg. Med. Chem. Lett. 2006, 16, 4141.
- (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 4141
- Pinto, D.J.P.¹ Orwat, M.J.² Quan, M.L.³ Han, Q.⁴ Galemmo, R.A.⁵ Amparo, E.⁶ Wells, B.⁷ Ellis, C.⁸ He, M.Y.⁹ Alexander, R.S.¹⁰ Rossi, K.A.¹¹ Smallwood, A.¹² Wong, P.C.¹³ Luettgen, J.M.¹⁴ Rendina, A.R.¹⁵ Knabb, R.M.¹⁶ Mersinger, L.¹⁷ Kettner, C.¹⁸ Bai, S.¹⁹ He, K.²⁰ Wexler, R.R.²¹ Lam, P.Y.S.²² more..

51
- 33748788587
- (d) Pinto, D. J. P.; Galemmo, R. A.; Quan, M. L.; Orwat, M. J.; Clark, C.; Li, R.; Wells, B.; Woerner, F.; Alexander, R. S.; Rossi, K. A.; Smallwood, A.; Wong, P. C.; Luettgen, J. M.; Rendina, A. R.; Knabb, R. M.; He, K.; Wexler, R. R.; Lam, P. Y. S. Bioorg. Med. Chem. Lett. 2006, 16, 5584.
- (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 5584
- Pinto, D.J.P.¹ Galemmo, R.A.² Quan, M.L.³ Orwat, M.J.⁴ Clark, C.⁵ Li, R.⁶ Wells, B.⁷ Woerner, F.⁸ Alexander, R.S.⁹ Rossi, K.A.¹⁰ Smallwood, A.¹¹ Wong, P.C.¹² Luettgen, J.M.¹³ Rendina, A.R.¹⁴ Knabb, R.M.¹⁵ He, K.¹⁶ Wexler, R.R.¹⁷ Lam, P.Y.S.¹⁸

52
- 49649127240
- Methyl 2-Hydroxy-4-isopropylamino-4-methyl- pentanoate (7a, yield: 86, A7Rf, CH2Cl2-MeOH, 19:1, 1HNMR(270 MHz, CDCl3, δ, 1.09, 1.11(2 x d, J= 6.3 Hz, 6 H, Me2CH, 1.19,1.27 (2 x s, 6 H, C qMe2, 1.72 (d, J, 6.6 Hz, 2 H, C qCH2, 2.99 (sept, J= 6.3 Hz, 1 H, CAMe 2, 3.75 (s, 3 H, OMe, 4.58 (t, J= 6.6 Hz, 1 H, OCH, 13C NMR (68 MHz, CDCl3, δ, 24.21, 28.88 (C qMe2, 25.79,26.35 (CHMe2, 42.64 (NCH, 43.11 (CHCH2, 51.59 (OMe, 54.32 (CqMe2, 69.52 (OCH, 174.39 (C=O, IR (NaCl, 3286, 1754 (OH, C=O) cm-1. MS (70 eV, m/z, no [M, 201 (15, 188 (33, M, Me, 186 (22, 171 (35, 170(15, 156(72, 144(11, 138(9, 128(24, 115 (13, 114 (38, 102 (12, 100 79, 99
- +-Me], 186 (22), 171 (35), 170(15), 156(72), 144(11), 138(9), 128(24), 115 (13), 114 (38), 102 (12), 100 (79), 99 (10), 98 (17), 96 (15), 86 (22), 85 (24), 84 (60), 83 (16), 74 (12), 72 (11), 71 (51), 70 (16), 68 (17), 58 (54), 57 (20), 56 (21), 55 (24).

53
- 49649092950
- 1-Isopropyl-3-methoxy-5,5-dimethylpiperidin-2-one (12, yield: 80, Rf0.40 (hexane-EtOAc, 3:2, 1HNMR (270 MHz, CDCl3, δ, 1.02, 1.05 (2 x s, 6 H, CqMe 2, 1.04, 1.06 (2 x d, J= 6.9 Hz, 6 H, Me2CH, 1.62 [dd, J= 7.0,13.0 Hz, 1 H, CqC#(H, 1.88 [dd, J= 8.0, 13.0Hz, 1 H, CqCH(H, 2.79 [d, J= 12.0 Hz, 1 H, NCH(H, 2.97 [d, J= 12.0 Hz, 1 H, NCH(H, 3.57 (s, 3 H, OMe, 3.87 (dd, J, 8.0. 13.0 Hz, 1 H, OCH, 4.87 (sept, J= 6.9 Hz, 1 H, CiMe2, 13C NMR (68 MHz, CDCl3, δ= 19.19, 19.43 (CHMe2, 26.04, 28.84 (CqMe2, 29.92 (CqCH2, 40.65 (CqCH2, 43.41 (CAMe2, 51.30 (NCH2, 58.85 (OMe, 75.96 (OCH, 169.13 (C=O, IR (NaCl, 1646 (C=O) cm-1. MS 70 eV, m/z, no [M
- 2: C, 66.29; H, 10.62; N, 7.03. Found: C, 66.13; H, 10.80; N, 6.88.

54
- 35348912513
- Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. J. Org. Chem. 2007, 72, 7980.
- (2007) J. Org. Chem , vol.72 , pp. 7980
- Alcaide, B.¹ Almendros, P.² Cabrero, G.³ Ruiz, M.P.⁴

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