Sodium Cyanide → tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, methanesulfonic acid (cis)-3-tert-butoxycarbonylamino-cyclopentylmethyl ester (crude from Step 4, 779 mg) was dissolved in DMF (5 ml). Potassium cyanide (277 mg, 4.25 mmol) was added and the reaction mixture was stirred at 80° C. overnight. Sodium cyanide (104 mg, 2.12 mmol) was added and the reaction mixture was stirred at 80° C. for 48 h. The reaction was cooled to room temperature, quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 190 mg (38%, 2 steps) of (cis-3-cyanomethyl-cyclopentyl)-carbamic acid tert-butyl ester as a light yellow oil.

Provenance & Evidence