Chloroiodomethane → Benzyl 2-azabicyclo[3.1.0]hexane-2-carboxylate

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Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester (example 4, step 5, 300 mg, 1.0 eq.) in diethyl ether was slowly added a solution of diethylzinc in hexanes (1M, 7 mL, 4.75 eq.), followed by chloroiodomethane (1.1 mL, 10 eq.). The reaction mixture was stirred 3 h at 0° C., allowed to warm up to room temperature and stirred an additional 3 h. The reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried over sodium sulphate and evaporated in vacuo and purified on silica, eluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane, to yield 160 mg (50%) of the desired product as colourless oil. MS (m/e): 218.5 (MH+, 100%)

Provenance & Evidence