Reaktion #489714

Reaktionsgleichung

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

→

title compound ( 32 )

Ausbeute 99.1%

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

Ausbeute 99.1%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed by filtration
2. 2
   Sonstigethe filtrate was evaporated in vacuo

Vorschrift

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+).

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