Hydrochloric Acid → ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionate

Participants

Reaction Steps

To a solution of ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (2.62 g) in ethanol (24 mL) and THF (12 mL) was added nickel(II) chloride hexahydrate (154 mg) under ice-cooling. Subsequently, sodium borohydride (489 mg) was added thereto under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added 1 M hydrochloric acid and water under ice-cooling. The resulting black solid was removed by filtration through Celite and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration, ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionate (2.82 g) was obtained as a colorless oily substance.

Provenance & Evidence