Ethanol → HCID 11256216, compound

Participants

Reaction Steps

To 72 mg (0.20 mmol) of 8-allyl-3-[(3-methoxy-phenyl)-thiophen-3-yl-methylene]-8-aza-bicyclo[3.2.1]octane in 2 mL of dichloromethane at −78° C. was added 1.68 mL ([1 M] in DCM) of boron tribromide drop wise. The reaction solution was slowly warmed to room temperature over 1 hr and allowed to stir 3 hr at room temperature. After 3 hr, to the reaction solution was added 4 mL of a saturated solution of NaHCO3, and 4 mL of 20% ethanol in DCM. The aqueous phase was removed. The organic phase was washed with 4 mL of brine, dried over MgSO4, and concentrated. The concentrated sample was purified by reverse phase chromatography (20×100 mm J'sphere H-80 YMC column using a gradient of 0.1% TFA/water to 5% water/0.1% TFA/acetonitrile). The eluent corresponding to 3-[(8-allyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-thiophen-3-yl-methyl]-phenol was evaporated to yield 12 mg of the title compound as a white solid; MS m/z (MH+) 338.

Provenance & Evidence