ISSN:
0947-3440
Keywords:
3-Methylpyrrolidines, N-alkylated
;
Pheromones
;
Reductions
;
Leptothoracine
;
Nitrogen heterocycles
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(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(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 (R)-1 by mesylation of (R)-8 is also described. Both enantiomers of 1 were obtained in excellent enantiomeric excesses (ee = 96%).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970217
