发明公开
EP0873298A4 CHIRAL REDUCTIONS OF IMINES LEADING TO THE SYNTHESES OF OPTICALLY ACTIVE AMINES
失效
手性削减了亚胺SYTHESE光学活性胺的LEAD
- 专利标题: CHIRAL REDUCTIONS OF IMINES LEADING TO THE SYNTHESES OF OPTICALLY ACTIVE AMINES
- 专利标题(中): 手性削减了亚胺SYTHESE光学活性胺的LEAD
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申请号: EP96933160申请日: 1996-09-27
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公开(公告)号: EP0873298A4公开(公告)日: 2000-05-17
- 发明人: VAN WAGENEN BRADFORD C , BARMORE ROBERT M
- 申请人: NPS PHARMA INC
- 专利权人: NPS PHARMA INC
- 当前专利权人: NPS PHARMA INC
- 优先权: US53546995 1995-09-28
- 主分类号: C07C209/44
- IPC分类号: C07C209/44 ; C07C209/52 ; C07C211/27 ; C07C211/29 ; C07C211/30 ; C07C213/02 ; C07C215/46 ; C07C217/54 ; C07C227/04 ; C07C229/38 ; C07C231/18 ; C07C237/30 ; C07C253/30 ; C07C255/58
摘要:
A process for preparing an R enantiomer of a compound of formula (I) wherein Me is methyl, Ar is 3-methoxyphenyl, 3-chlorophenyl, or 1-naphthyl, and X is independently selected from the group consisting of H, F, Cl, Br, I, phenyl, CF3, CF2H, CFH2, lower alkyl (e.g., Me), O-lower alkyl (e.g., OMe), OCH2CF3, OH, CN, NO2, C(O)-lower alkyl (e.g., C(O)Me), C(O)O-lower alkyl (e.g., C(O)OMe), C(O)NH-lower alkyl (e.g., C(O)NH-Me), C(O)N-lower alkyl2 (e.g., C(O)NMe2), OC(O)-lower alkyl (e.g., OC(O)Me), and NH-C(O)-lower alkyl (e.g., NH-C(O)Me), where "lower alkyl" is selected from a group consisting of 1 to 6 carbon atoms, and m is an integer between 1 and 5, by asymmetrically and enantioselectively reducing an imine with a reducing agent/chiral auxiliary agent complex so as to produce an enantiomeric excess of R enantiomer of the compound of formula (I) over the S enantiomer of the compound of formula (I). The process is especially useful to produce compounds (R)-(+)-N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorophenyl)propanamine and (R)-(+)-N-[1-(3-methoxyphenyl)ethyl]-3-(phenyl)propanamine. Enantiomeric excess of the R enantiomer over S enantiomer of greater than 65 % have been achieved.
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