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Synlett

Volumn , Issue 17, 2008, Pages 2601-2604

Diastereoselective synthesis of substituted 4-piperidones and 4-piperidols using a double mannich reaction

(4) Chan, Yinman a Guthmann, Holger a Brimble, Margaret A a Barker, David a

a UNIVERSITY OF AUCKLAND (New Zealand)

Author keywords

4 piperidones; Mannich reaction; Multicomponent reaction

Indexed keywords

4 PIPERIDOL DERIVATIVE; BETA KETO ESTER DERIVATIVE; BISAMINOL ETHER DERIVATIVE; ESTER; ETHER DERIVATIVE; ETHYL 1 BUTYL 3,5 DIMETHYL 4 OXOPIPERIDINE 3 CARBOXYLATE; ETHYL 1 BUTYL 3,5,5 TRIMETHYL 4 OXOPIPERIDINE 3 CARBOXYLATE; ETHYL 1 BUTYL 5 ETHYL 3 METHYL 4 OXOPIPERIDINE 3 CARBOXYLATE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; MANNICH REACTION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 55649090381 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083522 Document Type: Article

Times cited : (9)

References (43)

1
- 0034676585
- (a) Watson, P. S.; Jiang, B.; Scott, B. Org. Lett. 2000, 2, 3679.
- (2000) Org. Lett , vol.2 , pp. 3679
- Watson, P.S.¹ Jiang, B.² Scott, B.³

2
- 0034728886
- (b) Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. Tetrahedron Lett. 2000, 41, 3489.
- (2000) Tetrahedron Lett , vol.41 , pp. 3489
- Danieli, B.¹ Lesma, G.² Passarella, D.³ Silvani, A.⁴

3
- 84991695830
- (c) Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. J. Org. Chem. 1998, 63, 3492.
- (1998) J. Org. Chem , vol.63 , pp. 3492
- Danieli, B.¹ Lesma, G.² Passarella, D.³ Silvani, A.⁴

4
- 0035807571
- (d) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
- (2001) Org. Lett , vol.3 , pp. 3169
- Davis, F.A.¹ Chao, B.² Rao, A.³

5
- 0002603630
- (a) Manske, R. H. Can. J. Res. 1938, 16B, 57.
- (1938) Can. J. Res , vol.16 B , pp. 57
- Manske, R.H.¹

6
- 0002827686
- (b) Goodson, J. A. J. Chem. Soc. 1943, 139.
- (1943) J. Chem. Soc , pp. 139
- Goodson, J.A.¹

7
- 0007233555
- (c) Yunusov, M. S. Nat. Prod. Rep. 1993, 10, 471.
- (1993) Nat. Prod. Rep , vol.10 , pp. 471
- Yunusov, M.S.¹

8
- 0030474553
- (c) Hardick, D. J.; Blagbrough, I. S.; Cooper, G.; Potter, B. V. L.; Critchley, T.; Wonnacott, S. J. Med. Chem. 1996, 39, 4860.
- (1996) J. Med. Chem , vol.39 , pp. 4860
- Hardick, D.J.¹ Blagbrough, I.S.² Cooper, G.³ Potter, B.V.L.⁴ Critchley, T.⁵ Wonnacott, S.⁶

9
- 23644452620
- (a) Goodall, K. J.; Barker, D.; Brimble, M. A. Synlett 2005, 1809.
- (2005) Synlett , pp. 1809
- Goodall, K.J.¹ Barker, D.² Brimble, M.A.³

10
- 0031847559
- (b) Doisy, X.; Blagbrough, I. S.; Wonnacott, S.; Potter, B. V. L. Pharm. Pharmacol. Commun. 1998, 4, 313.
- (1998) Pharm. Pharmacol. Commun , vol.4 , pp. 313
- Doisy, X.¹ Blagbrough, I.S.² Wonnacott, S.³ Potter, B.V.L.⁴

11
- 0033516888
- (c) Bergmeier, S. C.; Lapinsky, D. J.; Free, R. B.; McKay, D. B. Bioorg. Med Chem. Lett. 1999, 9, 2263.
- (1999) Bioorg. Med Chem. Lett , vol.9 , pp. 2263
- Bergmeier, S.C.¹ Lapinsky, D.J.² Free, R.B.³ McKay, D.B.⁴

12
- 0037024561
- (d) Bryant, D. L.; Free, R. B.; Thomasy, S. M.; Lapinsky, D. J.; Ismail, K. A.; Arason, K. M.; Bergmeier, S. C.; McKay, D. B. Ann. N. Y. Acad. Sci. 2002, 971, 139.
- (2002) Ann. N. Y. Acad. Sci , vol.971 , pp. 139
- Bryant, D.L.¹ Free, R.B.² Thomasy, S.M.³ Lapinsky, D.J.⁴ Ismail, K.A.⁵ Arason, K.M.⁶ Bergmeier, S.C.⁷ McKay, D.B.⁸

13
- 0036158737
- (e) Bryant, D. L.; Free, R. B.; Thomasy, S. M.; Lapinsky, D. J.; Ismail, K. A.; McKay, S. B.; Bergmeier, S. C.; McKay, D. B. Neurosci. Res. 2002, 42, 57.
- (2002) Neurosci. Res , vol.42 , pp. 57
- Bryant, D.L.¹ Free, R.B.² Thomasy, S.M.³ Lapinsky, D.J.⁴ Ismail, K.A.⁵ McKay, S.B.⁶ Bergmeier, S.C.⁷ McKay, D.B.⁸

14
- 2942525659
- (f) Bergmeier, S. C.; Ismail, K. A.; Arason, K. M.; McKay, S.; Bryant, D. L.; McKay, D. B. Bioorg. Med Chem. Lett. 2004, 14, 3739.
- (2004) Bioorg. Med Chem. Lett , vol.14 , pp. 3739
- Bergmeier, S.C.¹ Ismail, K.A.² Arason, K.M.³ McKay, S.⁴ Bryant, D.L.⁵ McKay, D.B.⁶

15
- 0036592324
- (g) Ismail, K. A.; Bergmeier, S. C. Eur. J. Med. Chem. 2002, 469.
- (2002) Eur. J. Med. Chem , pp. 469
- Ismail, K.A.¹ Bergmeier, S.C.²

16
- 19944428573
- (h) Simoni, D.; Rossi, M.; Rondanin, R.; Baruchello, R.; Grisolia, G.; Eleopra, M.; Giovannini, R.; Bozzoli, A.; Davalli, S.; Di Fabio, R.; Donati, D. Tetrahedron Lett. 2005, 46, 759.
- (2005) Tetrahedron Lett , vol.46 , pp. 759
- Simoni, D.¹ Rossi, M.² Rondanin, R.³ Baruchello, R.⁴ Grisolia, G.⁵ Eleopra, M.⁶ Giovannini, R.⁷ Bozzoli, A.⁸ Davalli, S.⁹ Di Fabio, R.¹⁰ Donati, D.¹¹

17
- 41649097152
- (i) Huang, J.; Orac, C. M.; McKay, S.; McKay, D. B.; Bergmeier, S. C. Bioorg. Med Chem. 2008, 16, 3816.
- (2008) Bioorg. Med Chem , vol.16 , pp. 3816
- Huang, J.¹ Orac, C.M.² McKay, S.³ McKay, D.B.⁴ Bergmeier, S.C.⁵

18
- 37249032343
- Fustero, S.; Jimenez, D.; Moscardo, J.; Catalan, S.; del Pozo, C. Org. Lett. 2007, 9, 5283.
- (2007) Org. Lett , vol.9 , pp. 5283
- Fustero, S.¹ Jimenez, D.² Moscardo, J.³ Catalan, S.⁴ del Pozo, C.⁵

19
- 38349075661
- (a) Murty, M. S. R.; Ram, R.; Yadav, J. S. Tetrahedron Lett. 2008, 49, 1141.
- (2008) Tetrahedron Lett , vol.49 , pp. 1141
- Murty, M.S.R.¹ Ram, R.² Yadav, J.S.³

20
- 23944437477
- (b) Dobbs, A. P.; Guesne, S. J. J. Synlett 2005, 2101.
- (2005) Synlett , pp. 2101
- Dobbs, A.P.¹ Guesne, S.J.J.²

21
- 33748625993
- (c) Carballo, R. M.; Ramirez, M. A.; Rodriguez, M. L.; Martin, V. S.; Padron, J. I. Org. Lett. 2006, 8, 3837.
- (2006) Org. Lett , vol.8 , pp. 3837
- Carballo, R.M.¹ Ramirez, M.A.² Rodriguez, M.L.³ Martin, V.S.⁴ Padron, J.I.⁵

22
- 30144434127
- Sales, M.; Charette, A. B. Org. Lett. 2005, 7, 5773.
- (2005) Org. Lett , vol.7 , pp. 5773
- Sales, M.¹ Charette, A.B.²

23
- 20444481574
- Brimble, M. A.; Brocke, C. Eur. J. Org. Chem. 2005, 2385.
- (2005) Eur. J. Org. Chem , pp. 2385
- Brimble, M.A.¹ Brocke, C.²

24
- 33746917485
- Halliday, J. I.; Chebib, M.; Turner, P.; McLeod, M. D. Org. Lett. 2006, 8, 3399.
- (2006) Org. Lett , vol.8 , pp. 3399
- Halliday, J.I.¹ Chebib, M.² Turner, P.³ McLeod, M.D.⁴

25
- 53849127869
- (a) Kuthan, J.; Palecek, J. Collect. Czech. Chem. Commun. 1963, 28, 2260.
- (1963) Collect. Czech. Chem. Commun , vol.28 , pp. 2260
- Kuthan, J.¹ Palecek, J.²

26
- 55649110348
- US 20050176772
- (b) Calabrese, A. A.; Fradet, D. S.; Hepworth, D.; Lansdell, M. US 20050176772, 2005.
- (2005)
- Calabrese, A.A.¹ Fradet, D.S.² Hepworth, D.³ Lansdell, M.⁴

27
- 28844437779
- Davis, J. M.; Truong, A.; Hamilton, A. D. Org. Lett. 2005, 7, 5405.
- (2005) Org. Lett , vol.7 , pp. 5405
- Davis, J.M.¹ Truong, A.² Hamilton, A.D.³

28
- 13344291512
- (a) Howton, D. J. Org. Chem. 1945, 10, 277.
- (1945) J. Org. Chem , vol.10 , pp. 277
- Howton, D.¹

29
- 0038400209
- (b) McElvain, S. M. J. Am. Chem. Soc. 1926, 48, 2179.
- (1926) J. Am. Chem. Soc , vol.48 , pp. 2179
- McElvain, S.M.¹

30
- 0025815181
- (a) Dodd, D. S.; Oehlschlager, A. C. Tetrahedron Lett. 1991, 32, 3643.
- (1991) Tetrahedron Lett , vol.32 , pp. 3643
- Dodd, D.S.¹ Oehlschlager, A.C.²

31
- 33846452124
- (b) Khartulyari, A. S.; Maier, M. M. Eur. J. Org. Chem. 2007, 317.
- (2007) Eur. J. Org. Chem , pp. 317
- Khartulyari, A.S.¹ Maier, M.M.²

32
- 0006991873
- (c) Langiois, Y.; Potier, R. Tetrahedron 1975, 31, 423.
- (1975) Tetrahedron , vol.31 , pp. 423
- Langiois, Y.¹ Potier, R.²

33
- 0035813439
- Yoshizawa, K.; Toyota, S.; Toda, F. Tetrahedron Lett. 2001, 42, 7983.
- (2001) Tetrahedron Lett , vol.42 , pp. 7983
- Yoshizawa, K.¹ Toyota, S.² Toda, F.³

34
- 33847805890
- Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
- (1974) J. Am. Chem. Soc , vol.96 , pp. 1082
- Huckin, S.N.¹ Weiler, L.²

35
- 14844297700
- Misaki, T.; Nagase, R.; Matsumoto, K.; Tanabe, Y. J. Am. Chem. Soc. 2005, 127, 2854.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 2854
- Misaki, T.¹ Nagase, R.² Matsumoto, K.³ Tanabe, Y.⁴

36
- 0742313954
- (a) Kiguchi, T.; Hashimoto, C.; Naito, T.; Ninomiya, I. Heterocydes 1982, 19, 2279.
- (1982) Heterocydes , vol.19 , pp. 2279
- Kiguchi, T.¹ Hashimoto, C.² Naito, T.³ Ninomiya, I.⁴

37
- 4444237138
- (b) Horii, Z.; Watanabe, T.; Kurihara, T.; Tamura, Y. Chem. Pharm. Bull. 1965, 13, 420.
- (1965) Chem. Pharm. Bull , vol.13 , pp. 420
- Horii, Z.¹ Watanabe, T.² Kurihara, T.³ Tamura, Y.⁴

38
- 37049111095
- (c) Ninomyia, I.; Hashimoto, C.; Kiguchi, T.; Naito, T. J. Chem. Soc., Perkin Trans, 1 1985, 941.
- (1985) J. Chem. Soc., Perkin Trans, 1 , pp. 941
- Ninomyia, I.¹ Hashimoto, C.² Kiguchi, T.³ Naito, T.⁴

39
- 0141733703
- (a) Simonsen, K. B.; Ayida, B. K.; Vourloumis, D.; Winters, G. C.; Takahashi, M.; Shandrick, S.; Zhao, Q.; Hermann, T. ChemBioChem 2003, 4, 886.
- (2003) ChemBioChem , vol.4 , pp. 886
- Simonsen, K.B.¹ Ayida, B.K.² Vourloumis, D.³ Winters, G.C.⁴ Takahashi, M.⁵ Shandrick, S.⁶ Zhao, Q.⁷ Hermann, T.⁸

40
- 0033534520
- (b) Bach, P.; Lohse, A.; Bols, M. Tetrahedron Lett. 1999, 40, 367.
- (1999) Tetrahedron Lett , vol.40 , pp. 367
- Bach, P.¹ Lohse, A.² Bols, M.³

41
- 0034740249
- (c) Liang, X.; Petersen, B. O.; Duus, J.; Bols, M. J. Chem. Soc., Perkin Trans, 1 2001, 2764.
- (2001) J. Chem. Soc., Perkin Trans, 1 , pp. 2764
- Liang, X.¹ Petersen, B.O.² Duus, J.³ Bols, M.⁴

42
- 0026694889
- Beeson, C.; Pham,N.; Dix, T. A. Tetrahedron Lett. 1992, 43, 2925.
- (1992) Tetrahedron Lett , vol.43 , pp. 2925
- Beeson, C.¹ Pham, N.² Dix, T.A.³

43
- 55649103333
- General Procedure for the Synthesis of 4-Piperidones 5 Methyltrichlorosilane (1.5 mmol) was added dropwise to a mixture of β-keto ester 4 (1 mmol) and bisaminol ether 3 (1.2 mmol) in dry MeCN (3 mL) then stirred at r.t. for 20 h. The reaction was then quenched with aq sat. NaHCO3 until basic, extracted with EtOAc (3 × 3 mL, dried (MgSO4, and concentrated in vacuo to give the crude product, which was purified by flash chromatography to afford the 4-piperidones 5 in 51-90% yields. General Procedure for the Synthesis of 4-Piperidols 6 A solution of piperidone 5 (1 mmol) in THF (4 mL) was added to a solution of NaBH4 (0.5 mmol) in THF (4 mL) and deionized H2O (4 mL, The mixture was stirred for 30 min at 0 °C, then stirred for 3 h at r.t. The reaction was quenched with 2 M NaOH and extracted with Et2O (3 × 10 mL, The combined organic extracts were washed with brine, dried MgSO4
- 3), 2.53 (2 H, t, J = 6.9 Hz

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