Reacción #52209

Ecuación de reacción

hydrochloric acid

Diisobutylaluminium hydride

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoate

methanol

→

title compound

tert-Butyl (1S)-1-(3-fluorophenyl)-3-oxopropylcarbamate

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred for 30 minutes
2. 2
   Temperaturato warm up to room temperature
3. 3
   Otrothe layers were separated
4. 4
   Secadothe organic layer was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated under reduced pressure

Procedimiento

Diisobutylaluminium hydride (1 M in dichloromethane, 39 ml, 39 mmol) was cooled to −78° C. and added dropwise to a solution of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoate (WO 0039125) (5.4 g, 18.2 mmol) in dichloromethane (100 ml) at −78° C. The reaction was stirred for 30 minutes at −78° C., then methanol (50 ml, pre-cooled to −78° C.) was added. The reaction was stirred for 30 minutes, then 2 N hydrochloric acid (250 ml) added. The bi-phasic mixture was allowed to warm up to room temperature, the layers were separated, and the organic layer was dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound as a clear, colourless oil, 4.8 g.

Fuente