Reacción #11344

Ecuación de reacción

potassium hydroxide

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol

→

3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane

Rendimiento 77.3%

Disolventes

dichloromethane

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   Otroto give a white solid
3. 3
   Lavadowashed with water
4. 4
   Secadodried over anhyd MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otroto give a white solid
7. 7
   OtroThe solid was crystallized from hexanes and ethyl acetate

Procedimiento

A solution of potassium hydroxide (6.52 g, 0.116 mol, 1.2 equiv.) in 970 mL of absolute ethanol was treated with N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (32.3 g, 0.097 mol). This solution was stirred at room temperature for 15 minutes and then concentrated in vacuo to give a white solid. The solid was dissovled in dichloromethane and washed with water, dried over anhyd MgSO4, filetered and concentrated in vacuo to give a white solid. The solid was crystallized from hexanes and ethyl acetate to give 22.3 g, 77% of 3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane, mp 102–103° C., FAB MS: MH+=298.

Fuente