tert-butyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate → tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 0° C. cold solution of 2.00 g N-Boc-nortropinone in 50 mL of methanol was added portionwise 672 mg of sodium borohydride. The reaction mixture was stirred at 0° C. for 1 h. The solvent was evaporated, the crude product was taken up in dichloromethane and treated with sat. sodium bicarbonate solution. The phases were separated and the aqueous phase extracted twice with dichloromethane. The organic phases were combined, dried over magnesium sulfate and concentrated to give 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (70) as diastereomeric mixture. Rt=1.11 min, 1.17 min (Method C). Detected mass: 128.0 (M-Boc+H+).

Provenance & Evidence