SCOPUS 정보 검색 플랫폼

Volumn 11, Issue 18, 2000, Pages 3659-3663

Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

(6) Fang, Qun K a Han, Zhengxu a Grover, Paul a Kessler, Donald a Senanayake, Chris H a Wald, Stephen A a

a SUNOVION PHARMACEUTICALS INC (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMFEBUTAMONE; DRUG METABOLITE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0034703153 PISSN: 09574166 EISSN: None Source Type: Journal
DOI: 10.1016/S0957-4166(00)00349-9 Document Type: Article

Times cited : (94)

References (25)

1
- 0023119211
- and references cited therein.
- (1987) Xenobiotica , vol.17 , pp. 287
- Welch, R.F.¹ Lai, A.A.² Schroeder, D.H.³

2
- 0030065670
- (1996) J. Med. Chem. , vol.39 , pp. 347-349
- Kelley, J.L.¹ Musso, D.L.² Boswell, G.E.³ Soroko, F.E.⁴ Cooper, B.R.⁵

3
- 0027433142
- (1993) Chirality , vol.5 , pp. 495
- Musso, D.L.¹ Mehth, N.B.² Soroko, F.E.³ Ferris, R.M.⁴ Hollingsworth, E.B.⁵ Kenney, B.T.⁶

4
- 0007406601
- (1997) Bioorg. Med. Chem. Lett. , pp. 1
- Musso, D.L.¹ Mehth, N.B.² Soroko, F.E.³

5
- 0031803596
- (1998) Chirality , pp. 307
- Mey, B.¹ Paulus, H.² Lamparter, E.³ Blaschke, G.⁴

6
- 0030913764
- and references cited therein.
- (1997) Biomed. Chromatogr. , vol.11 , pp. 174
- Suckow, R.F.¹ Zhang, M.F.² Cooper, T.B.³

7
- 0031418125
- (1997) J. Heterocycl. Chem. , vol.34 , pp. 1813
- Boswell, G.E.¹ Musso, A.O.² Davis, D.L.³ Kelley, J.L.⁴ Soroko, F.E.⁵ Cooper, B.R.⁶

8
- 0007359082
- Due to the presence of chlorine substitution (meta) on the phenyl ring and the t-butylamine substitution on the side chain, common methods for the synthesis of arylketone (e.g. Friedel-Crafts reaction with enantiomerically enriched acid chloride) are not applicable to bupropion synthesis.

9
- 0000882040
- (1992) J. Org. Chem. , vol.57 , pp. 5067-8
- Hashiyama, T.¹ Morikawa, K.² Sharpless, K.B.³

10
- 0032481328
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 708
- Adam, W.¹ Fell, R.T.² Stegmann, V.R.³ Saha-Moller, C.R.⁴

11
- 0000043848
- (1992) Chem. Rev. , vol.92 , pp. 919
- Davis, F.A.¹ Chen, B.C.²

12
- 0000227155
- (1990) J. Am. Chem. Soc. , pp. 6679
- Davis, F.A.¹ Sheppard, A.C.² Chen, B.C.³

13
- 0027179113
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1793
- Duh, T.H.¹ Wang, Y.F.² Wu, M.J.³

14
- 0001646817
- (1992) J. Org. Chem. , vol.57 , pp. 1526
- Bradshaw, C.W.¹ Fu, H.² Shen, G.J.³ Wong, C.H.⁴

15
- 0033611957
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4080
- Zhu, Y.¹ Manske, K.J.² Shi, Y.³

16
- 0032558662
- (1998) Tetrahedron Lett. , vol.39 , pp. 7819
- Zhu, Y.¹ Tu, Y.² Yu, H.³ Shi, Y.⁴

17
- 0007357580
- Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Synthesis; Wiley-VCH: Weinheim, 1997

18
- 84985204984
- (1986) Liebigs Ann. Chem. , pp. 334
- Effenberger, F.¹ Burkard, U.²

19
- 0007359412
- (1984) Angew. Chem. , vol.84 , pp. 798
- Kunz, H.¹ Lerchen, H.G.²

20
- 0031019842
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 253
- Giordani, A.¹ Carera, A.² Pinciroli, V.³ Cozzi, P.⁴

21
- 0026638808
- Synthesis of chiral ketone traflate has been reported and has been used for the preparation of chiral α-fluoroketone
- (1992) J. Med. Chem. , vol.35 , pp. 2113
- Liu, A.¹ Carlson, K.E.² Katzenellenbogen, J.A.³

22
- 0000224979
- and references cited therein.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 5568
- Creary, X.¹

23
- 0007358859
- In order to obtain high ee's of hydroxyketone TBS ether is crucial; when TMS was used 93% ee was obtained in the ADH reaction. When the TBS enol ether is replaced with vinyl chloride, the ee of the hydroxy ketone was 90%

24
- 0007359250
- 1H NMR data was identical to the racemate sample. Ee's were analyzed with ChiralPAK® AD column eluted with hexane/IPA/DEA (99/1/0.1). (R)-(-)-Isomer, 4.51 min; (S)-(+)-isomer, 5.66 min. (Absolute configuration of (S)-bupropion is established on AD chemistry.) Also see Ref. 14, which is further confirmed by X-ray analysis.

25
- 0007443382
- note

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.