Diazomethane → HCID 86691260, compound

Participants

Reaction Steps

Prepare an ethanol free solution of diazomethane in diethyl ether from a solution of potassium hydroxide (3.2 g, 57 mmol) in water (5 mL), diethylene glycol monoethyl ether (4 mL) and diethyl ether (10 mL) and N-methyl-N′-nitro-N-nitrosoguanidine (5 g, 34 mmoles) in a mixture of diethyl ether (35 mL) and diethylene glycol monoethyl ether (15 mL). Take the resulting solution of diazomethane and add it portionwise over 60 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 (185 mg) in diethyl ether (2 mL). Once gas evolution has ceased, leave to stand for 30 minutes, filter and concentrate under reduced pressure to yield a yellow oil. Purify by mass guided HPLC (RT=6.4 minutes (UV), 6.37 minutes (MS); LC Column: Waters XBridge™ 30 mm×100 mm Sum; water w/0.1% formic acid; gradient: 28-62% acetonitrile w/0.1% formic acid in 1.35 minutes then 62-95% in 6.65 minutes, then held at 95% for 3.55 minutes. Column temperature: ambient; flow rate: 45 mL/minute) to yield the title compound as a colorless oil (55.3 mg, 130.6 μmol). MS (m/z): 446 (M+23).

Provenance & Evidence