Dimethyl Sulfoxide → 4-[(1R,7aS)-1-Methyl-3,7-dioxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of DMSO (20 μL) in CH2Cl2 (1 mL) at −78° C. was added oxalyl chloride (1.0 M in CH2Cl2, 131 μL). This mixture was stirred at −78° C. for 30 min. and then a solution of 61K in CH2Cl2 (20 mg in 1 mL). The reaction was stirred at −78° C. for 1 h and then i-Pr2NEt (100 μL) was added and the reaction was allowed to warm to rt over 1 h. The reaction was extracted with EtOAc and washed twice with 1N HCl and once with saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 40% EtOAc/CH2Cl2) provided the title compound (18 mg): MS (ES) m/z 304.42 [M+H]+

Provenance & Evidence