3-Aminopyrrolidines from alpha-aminoacids: total synthesis of (+)-nemonapride from D-alanine.
The antipsychotic compound nemonapride 1 was synthesized in nine steps from d-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.
Hoang
Cam Thuy
CT
Laboratoire de Chimie des Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS No. 8182), Université Paris-Sud, F-91405 Orsay, France.
Nguyen
Viet Hoang
VH
Alezra
Valérie
V
Kouklovsky
Cyrille
C
D000409:Alanine / Q000737:chemistry*; D000586:Amination; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*
D001549:Benzamides; D011763:Pyrrolizidine Alkaloids; D000409:Alanine; C030265:nemonapride