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Simple Synthesis of Both Enantiomers of 3‐Methyl‐ N ‐(3‐Methylbutyl)pyrrolidine
Author(s) -
Veith Hans Jürgen,
Collas Markus,
Zimmer Reinhold
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970217
Subject(s) - pyrrolidine , enantiomer , chemistry , ring (chemistry) , halogenation , stereochemistry , organic chemistry
( S )‐3‐Methyl‐ N ‐(3‐methylbutyl)pyrrolidine ( 1 ) and its antipode ( R )‐ 1 have been prepared by reduction of ( S )‐4,5‐dihydro‐3‐methyl‐2(3 H )furanone ( 7 ) and dimethyl ( R )‐2‐methylsuccinate ( 11 ), bromination thereof, and ring closure of the intermediates ( S )‐ 9 and ( R )‐ 9 , respectively, with 3‐methylbutylamine ( 10 ). An alternative synthesis of ( R )‐ 1 by mesylation of ( R )‐ 8 is also described. Both enantiomers of 1 were obtained in excellent enantiomeric excesses ( ee = 96%).