Simple synthesis of both enantiomers of 3-methyl-N-(3-methylbutyl)pyrrolidine

Article abstract of DOI:10.1002/jlac.199719970217

(S)-3-Methyl-N-(3-methylbutyl)pyrrolidine (1) and its anti-pode (R)-1 have been prepared by reduction of (S)-4,5-dihydro-3-methyl-2(3H)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 (A)-1 by mesylation of (R)-8 is also described. Both enantiomers of 1 were obtained in excellent enantiomeric excesses (ee = 96%). VCH Verlagsgesellschaft mbH, 1997.