Diethyl Ether → Di-tert-butyl (1S,2R,5R,6R)-2-(tert-butoxycarbonylamino)-3-(dimethylaminomethylene)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of di-tert-butyl (1S,2S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (15.15 g, 36.82 mmol, See WO03/104217/A2 for synthesis details) in toluene (90.90 mL) is added tert-butoxybis(dimethylamino)methane (12.83 g, 73.63 mmol). This mixture is then heated to 80° C. for 1 hour and then allowed to cool to ambient temperature. The solvent volume is reduced to about 35 ml. The mixture is stirred while diethyl ether and hexane are added to cause a precipitate to form. The solids are collected by filtration, washed with hexanes, and air dried to obtain the title compound (16.7 g, 35.79 mmol, 97.2% yield). MS (m/z): 467.2 (M+H).

Provenance & Evidence