Reaktion #2016678

Reaktionsgleichung

(2RS)-bromo-N-[(RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-3-phenyl-propionamide

potassium

butylate

(2R,5S)-2-benzyl-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one

(2S,5R)-2-benzyl-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one

→

N-[(RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-3-phenyl-acrylamide

Ausbeute 30.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn analogy to the cyclization reaction
2. 2
   Sonstigedescribed for the preparation of Building block C

Vorschrift

In analogy to the cyclization reaction described for the preparation of Building block C, the reaction of (2RS)-bromo-N-[(RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-3-phenyl-propionamide with potassium tent-butylate yielded besides the N-[(RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-3-phenyl-acrylamide (0.381 g, 30% of theory), (2R,5S)-2-benzyl-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one and (2S,5R)-2-benzyl-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one as the dominant diastereoisomer in form of a white foam (51% of theory). Mass (calculated) C18H17BrFNO2[378.244]; (found) [M+H]+=378, [M+2-H]+=380.

Quelle