Sodium Bicarbonate → HCID 66727794, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1RS,5SR,6RS)-2-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid ethyl ester (172 mmole) in MeOH (900 ml) was subsequently added NaHCO3 (33.25 g) and magnesium-monoperoxyphthalate (104.5 g) and stirring was continued at ambient temperature for 1 h. The mixture was filtered, the filtrate evaporated and the residue partitioned between saturated NaHCO3 (until gas evolution ceased) and dichloromethane. The organic layer was dried, evaporated and the residue dissolved in MeOH (750 ml). To the solution was subsequently added water (65 ml) and p-toluenesulfonic acid hydrate (3.44 g) and the mixture was stirred at 22° C. for 18 h. The mixture was evaporated, the residue partitioned between saturated NaHCO3 and dichloromethane, the organic layer was dried, evaporated and the residue dissolved in diethylether (350 ml) at reflux temperature. The solution was treated with n-pentane until the solution became cloudy, the mixture was slowly cooled to 0° C. and stirring was continued at 0° C. for 2 h. The suspension was filtered, and the residue dried to give the title compound (15.0 g) as white crystals.

Provenance & Evidence