3-Quinuclidinone → 3-Quinuclidinol, (+)-

Participants

Reaction Steps

In an autoclave (160 ml), a solution of 200 mg (0.41 mmol) of bis(1,5-cyclooctadiene)dirhodium(I) dichloride and 480 mg (0.81 mmol) of (R)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyl-dicyclohexylphosphine (IIIb, corresponding to an educt/catalyst molar ratio of 50) in 70 ml of degassed methanol was added to 5.00 g (40 mmol) of 3-quinuclidinone under argon. The mixture was hydrogenated for 22 hours at 75° C. and 50 bar of H2. After evaporation of the reaction solution, the pH was adjusted to 1 with 1N hydrochloric acid and the mixture was extracted three times with 50 ml of dichloromethane. The aqueous phase was adjusted to pH 14 with sodium hydroxide solution (30 percent) and evaporated to dryness. The residue was extracted four times with 100 ml of dichloromethane and the combined organic extracts were dried over MgSO4 and evaporated to give 3.40 g (67 percent) of (S)-3-quinuclidinol in the form of a white crystalline solid. Recrystallization from ethyl acetate gave 2.65 g (52 percent) of (S)-3-quinuclidinol with 7 percent ee. Other data concerning the product was: ##EQU7##

Provenance & Evidence