Sodium borohydride → HCID 86596972, compound

Participants

Reaction Steps

Examples 11p and 11q, Step 3: To a solution of tert-butyl 2-(dibenzylamino)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (3.12 g, 7.42 mmoles) in 50 ml of THF and 10 ml of water was added sodium borohydride (1.4 g, 37.1 mmoles), and the mixture was stirred for 6 hours at room temperature. The reaction was quenched with saturatedd sodium bicarbonate, and the product was extracted with EtOAc three times. The combined extracts were washed with brine, dried over Na2SO4 and evaporated to give an oily residue. It was purified by column chromatography (silica gel, 3:7 EtOAc and hexane) to give 2.28 g of tert-butyl (1R,3R,4S)-4-(dibenzylamino)-3-(hydroxymethyl)cyclohexylcarbamate as an oil.

Provenance & Evidence