SYNTHESIS OF (R) AND (S)-3-AMINOQUINUCLIDINE FROM 3-QUINUCLIDINONE AND (S) AND (R)-1-PHENETHYLAMINE

被引:17
作者
LANGLOIS, M
MEYER, C
SOULIER, JL
机构
[1] CNRS-CERCOA, F-94320, THIAIS
关键词
D O I
10.1080/00397919208021320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of (R) and (S)-3-amino quinuclidine, an important building block for the synthesis of chiral 5-HT3 serotonin receptor antagonists, is described. The key reaction is the reduction by NaBH4 of the imine prepared from the 3-quinuclidinone and chiral (S) or (R)-1-phenethylamine.
引用
收藏
页码:1895 / 1911
页数:17
相关论文
共 22 条
[1]   CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF N-CONTAINING NATURAL-PRODUCTS .4. A FACILE METHOD FOR THE ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE 1-(2-FLUOROPHENYL)-ETHYLAMINE [J].
BRINGMANN, G ;
GEISLER, JP .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 49 (01) :67-73
[3]  
BRINGMANN G, 1990, LIEBIGS ANN CHEM, P795
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]   DICHLOROMETHANE AS REACTANT IN SYNTHESIS - AN EXPEDIENT TRANSFORMATION OF PROLINAMIDE TO A NOVEL PYRROLO[1,2-C]IMIDAZOLONE [J].
FEDERSEL, HJ ;
KONBERG, E ;
LILLJEQUIST, L ;
SWAHN, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2254-2256
[6]  
FITZPATRICK LR, 1990, J PHARMACOL EXP THER, V254, P450
[7]  
FUKUDA T, 1991, EUR J PHARMACOL, V196, P299
[8]  
GOZLAN H, 1992, IN PRESS CENTRAL PER
[9]  
IMBERT T, 1983, Patent No. 834013385
[10]  
Kaiser A., 1947, HELV CHIM ACTA, V50, P2170