Simple Synthesis of Both Enantiomers of 3-Methyl-N-(3-Methylbutyl)pyrrolidine

(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‐methylbutylamin...

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Veröffentlicht in:Liebigs Annalen 1997-02, Vol.1997 (2), p.391-394
Hauptverfasser: Veith, Hans Jürgen, Collas, Markus, Zimmer, Reinhold
Format: Artikel
Sprache:eng
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Zusammenfassung:(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%).
ISSN:0947-3440
1099-0690
DOI:10.1002/jlac.199719970217