Sodium Azide → HCID 86607259, compound

Participants

Reaction Conditions

Reaction Steps

A solution of bromide (a) (52.4 g, 221 mmol) in DMF (1.2 liters) was treated with sodium azide (21.5 g, 331 mmol) and heated at 60° C. for 8 hours. The mixture was stirred at room temperature overnight and then evaporated. The residue was extracted with warm iso-propanol (2×300 ml). Evaporation afforded an oil which was chromatographed on silica eluting with a gradient of ethyl acetate in petroleum ether affording an oil (31 g) which was a 2:1 mixture of desired (1R,3R,4R)-4-azido-3-hydroxy-cyclohexanecarboxylic acid methyl ester to (R)-3-oxo-cyclohexanecarboxylic acid methyl ester. Further chromatography on silica eluting with a methanol/dichloromethane gradient afforded the desired intermediate as an oil (18.4 g, 42%)

Provenance & Evidence