tert-Butanol → HCID 68615579, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 150 mg (0.46 mmol) of (RS)-(E)-1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidine-3-carboxylic acid in 2 ml of tetrahydrofurane is cooled to −15° C. and 63 mg (0.46 mmol) of isobutyl chloroformate are added dropwise. After 5 min, a solution of 60 mg (0.92 mmol) of sodium azide in 0.5 ml water is added. The mixture is stirred at 0° C. for 45 min, then left to warm to RT. Toluene is added and the diluted solution is washed with a saturated solution of sodium hydrogencarbonate. The organic layer is separated, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is dissolved in 5 ml of toluene and the solution warmed to 80° C. After 30 min, 1.1 ml (1.2 mmol) of tert-butanol are added and heating is continued for 18 hours. For the working-up, the reaction mixture is evaporated and the crude product directly chromatographed on silica gel using a 95:5-mixture of dichloromethane and methanol as the eluent. After crystallisation from ether, 104 mg (57% of theory) of (RS)-(E)- (1-{4-[2-(3-fluoro-phenyl)-vinyl]-phenyl}-5-oxo-pyrrolidin-3-yl)-carbamic acid tert-butyl ester are obtained as a light yellow solid; MS: m/e=397 (M+H)+.

Provenance & Evidence