Dimethyl Sulfoxide → HCID 68907555, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylsulfoxide (6.8 ml) was added to a solution of oxalyl chloride (8.2 ml) in dichloromethane (100 ml) at −60° C., and a solution of (1R*,2S*)-N1,N2-bis(tert-butoxycarbonyl)-4-hydroxy-1,2-cyclohexanediamine (mixture of stereoisomers) (6.32 g) in tetrahydrofuran (80 ml) was added at a time, and the mixture was stirred for 1 hour. The temperature of the mixture was raised to −40° C., and triethylamine (21 ml) was added. The mixture was heated to room temperature. After 3 hours, the reaction mixture was poured into water and extracted with dichloromethane. The resultant organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (3.8 g) as a pale yellow solid.

Provenance & Evidence