Ammonia → Methyl-(2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-carbamic acid tert-butyl ester

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Reaction Steps

To a flame dried 125 mL rbf equipped with a dry ice condenser was added fresh sodium metal (0.32 g, 14.0 mmol). The flask was immersed in a −78° C. bath and ammonia gas was condensed into the flask until it was about a third full. The starting material methyl-[2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (Intermediate 9) (0.62 g, 1.40 mmol) in THF (10 mL) was added to the flask in a thin constant stream and the mixture was stirred for 10 minutes at which point tlc indicated the reaction was complete. Solid ammonium chloride was added cautiously and the reaction warmed to room temperature. The volatile solvents were allowed to evaporate and the residue was partitioned between 1N NaOH and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give methyl-(2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-carbamic acid tert-butyl ester as an oil (0.40 g, quantitative yield).

Provenance & Evidence