Simple Synthesis of Both Enantiomers of 3‐Methyl‐ N ‐(3‐Methylbutyl)pyrrolidine | Zendy

Veith Hans Jürgen | Zendy; Collas Markus | Zendy; Zimmer Reinhold | Zendy

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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%).

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