[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-thienyl]acetate → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-(hydroxymethyl)-2-thienyl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-thienyl]acetate (400 mg, 0.65 mmol) in pyridine (5 mL) was added HF.pyridine (0.88 mL) drop wise. The resultant solution was stirred at room temperature for 3 h. The reaction solution was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate (5 mL). The aqueous phase was extracted with ethyl acetate (3×10 mL) and the organic phases combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow solid (270 mg, 84%) which was used in the next step without further purification.

Provenance & Evidence