Boron trifluoride etherate → HCID 12051716, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 6-benzyl-7-hydroxy-3-phenyl-(3S, 7aR)-perhydroimidazo[1,5-C][1,3]thiazol-5-one of formula (6) (0.326 parts, 1 mmol) in dichloromethane (10 parts) was added 1,2-bistrimethylsilyloxy cyclohexene (0.516 parts, 2 mmol). Then the solution was cooled to 0° C. and Lewis acid for example BF3.Et2O (0.142 parts, 1 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 10 mints. and the reaction mixture was quenched with saturated ammonium chloride (10 parts). Then the organic layer was separated, concentrated and column purification with ethylacetate:pet.ether (15:85) as eluent provided compound 6-benzyl-7-(1-trimethylsilyloxy-2-oxocyclohexyl)-3-phenyl-(3S, 7R, 7aR)-perhydroimidazo[1,5-C][1,3]thiazole-5-one of formula (7e) (viscous liquid, 0.376 parts, 0.76 mmol) in 76% yield. And with ethyl acetate:pet.ether (25:75) as eluent provided the compound 6-benzyl-7-(1-hydroxy-2-oxocyclohexyi)-3-phenyl-(3S, 7R, 7aR)-perhydroimidazo[1,5-C][1,3]thiazole-5-one of formula (7e′) (highly viscous liquid, 0.093 parts. 0.22 mmol) in 22% yield.

Provenance & Evidence