Reacción #489714

Ecuación de reacción

(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol

→

title compound ( 32 )

Rendimiento 99.1%

(1R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-cyclopentanol

Rendimiento 99.1%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe catalyst was removed by filtration
2. 2
   Otrothe filtrate was evaporated in vacuo

Procedimiento

A solution of 2.0 g (9.33 mmol) of (1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol (Curran, et al. Tetrahedron 1997, 53, 1983-2004) in 10 mL of ethyl acetate was treated with 66 mg of 20% palladium hydroxide on activated carbon and the mixture was stirred overnight under a hydrogen atmosphere (1 atm) at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated in vacuo to give 2.0 g of the title compound (32). Rt=1.72 min (Method C). Detected mass: 217.2 (M+H+).

Fuente