Asymmetric synthesis of (+)-(S,S)-reboxetine via a new (S)-2-(hydroxymethyl)morpholine preparation.
(S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps. Key steps were selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution. [structure: see text]
Brenner
Eric
E
Yale School of Medicine, VA Connecticut HCS (116A2), West Haven, CT 06516, USA.
Baldwin
Ronald M
RM
Tamagnan
Gilles
G
D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D009025:Morpholines / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D000077593:Reboxetine; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009025:Morpholines; D000077593:Reboxetine