tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylate

Participants

Reaction Steps

3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester (8 g, 35.5 mmol) was dissolved in 100 mL of ethanol. Sodium borohydride (2 g, 53.5 mmol) was added to the solution portionwise at room temperature. After stirring for 3 hours, the reaction was evaporated in vacuo to give clear viscous oil. The oil was dissolved in dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford 7.55 g of 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester as a white crystalline solid; 1H NMR (300 MHz, DMSO-d6): 4.23 (dd, J=2.7, 4.6 Hz, 1 H), 4.18-4.06 (m, 2 H), 2.17-2.06 (m, 1 H), 1.99-1.91 (m, 3 H), 1.72-1.50 (m, 5H), 1.47 (s, 9H).

Provenance & Evidence