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Resolution and absolute configuration of 1,2,3,5,6,10bβ‐hexahydro‐6α‐phenylpyrrolo[2,1‐α]isoquinoline (McN‐4612‐Z). A problem of determination of the enantiomeric purity for a tertiary amine
Author(s) -
Maryanoff Bruce E.,
Mccomsey David F.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220359
Subject(s) - chemistry , enantiomer , absolute configuration , isoquinoline , diastereomer , resolution (logic) , optical rotation , stereochemistry , enantiomeric excess , amine gas treating , tertiary amine , specific rotation , enantioselective synthesis , organic chemistry , artificial intelligence , computer science , catalysis
Abstract Details for the resolution of 1,2,3,5,6,10bβ‐hexahydro‐6α‐phenylpyrrolo[2,1‐α]isoquinoline (1) , a potent antidepressant‐like compound, into its enantiomers with di‐ p ‐toluoyltartaric acid ( 2) are reported. Enantio‐merically‐enriched R ‐(+)‐2‐phenylpyrrolidine was transformed into enantiomerically‐enriched 1 to determine enantiomeric purity and absolute stereochemistry for the resolved amines 1 . Thus, we ascertain that samples of (+)‐ and (—)‐ 1 with an enantiomeric purity of ≥99% were prepared, and that bioactive (+)‐ 1 possesses the 6 S ,10b R absolute configuration. The enantiomeric purity of ≥99% was confirmed by 360‐MHz 1 H nmr examination of 1:1 diastereomeric salts formed from 1 or (—)‐ 1 and (+)‐Mosher's acid (MTPA). The maximal optical rotation reported (ref 8) for (+)‐ 3 (100% o.p.) was shown to correspond to 100% e.e.