tert-Butanol → tert-Butyl (3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

Participants

Reaction Steps

A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride (101 mg, 0.40 mmol), triethylamine (185 mg, 1.83 mmol), DPPA (180 mg, 0.65 mmol), t-butanol (4 ml) and toluene (3 ml) was heated under reflux in a nitrogen atmosphere for 23 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of sodium carbonate, water and a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (27 mg, 0.09 mmol, 24%).

Provenance & Evidence