Reaktion #1330390

Reaktionsgleichung

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

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was then filtered
2. 2
   Einengenconcentrated to a small volume
3. 3
   Sonstigepurified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient

Vorschrift

A solution of (+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol (1.43 g, 6.67 mmol) (from Example 29a supra) and Wilkinson's catalyst (1.23 g, 1.33 mmol) (Aldrich) in toluene (55 mL) was subjected to atmospheric pressure hydrogenation for 16.5 hours. The reaction mixture was then filtered, concentrated to a small volume, and purified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient to give (+)-(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless oil. (Yield 745 mg, 61%).

Quelle