Methyl iodide → Methyl-[2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

The starting material, racemic [2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (Intermediate 8) (0.6 g, 1.4 mmol) was slurried in DMF (5 mL) and the mixture was cooled to 0° C. Sodium hydride (oil free, 0.05 g, 2.1 mmol) was added in portions and the reaction was then stirred for 0.75 hours at room temperature. Methyl iodide (0.13 mL, 2.1 mmol) was added and the reaction stirred an additional hour at room temperature. The mixture was partitioned between 1N lithium chloride solution and EtOAc. The organics were washed with brine and dried over calcium sulfate, filtered and concentrated to give methyl-[2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester as a yellow crystalline solid (0.654 g, 105%) which contained approximately 0.33 mol % of DMF by 1HNMR.

Provenance & Evidence