Diazomethane → HCID 86691260, compound

Participants

Reaction Steps

Prepare an ethanol free solution of diazomethane in diethyl ether from a solution of potassium hydroxide (2.5 g, 44.6 mmol) in water (4 mL), diethylene glycol monoethyl ether (14 mL) and diethyl ether (8 mL) and N-methyl-N′-nitro-N-nitrosoguanidine (4 g, 27.2 mmol) in a mixture of diethyl ether (30 mL) and diethylene glycol monoethyl ether (15 mL). Take the resulting solution of diazomethane and add it portion wise over 30 minutes to a suspension of palladium acetate (20 mg, 89.1 μmol) in a solution of the previously prepared mixture of unreacted ditert-butyl (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)-4-methylene-bicyclo[3.1.0]hexane-2,6-dicarboxylate and title compound (260 mg) in diethyl ether (3 mL). Once gas evolution has ceased, leave to stand overnight, then filter through a phase separator frit and concentrate under reduced pressure to yield a dark oil. Purify by flash chromatography eluting with ethyl acetate:iso-hexane (0:100 to 75:25) to yield 185 mg of a mixture of unreacted ditert-butyl (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)-4-methylene-bicyclo[3.1.0]hexane-2,6-dicarboxylate and title compound.

Provenance & Evidence