Water → 2-t-Butoxycarbonyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine

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Reaction Conditions

Reaction Steps

A 2.00 g (8.86 mmol) portion of 3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine hydrochloride was dissolved in a mixed solvent of 70 ml chloroform and 10 ml methanol, and the solution was mixed with 3.67 g (26.58 mmol) of potassium carbonate and cooled to 0° C. This was mixed with 2.24 ml (9.75 mmol) of di-t-butyl bicarbonate and stirred overnight at room temperature. The reaction solution was poured into ice-cooled water and extracted with chloroform. The extract was washed with water and dried (Na2SO4), and then the solvent was removed by evaporation under a reduced pressure and the thus obtained oily material was purified by a silica gel column chromatography (250 cc; elution by ethyl acetate-hexane=1:6) to obtain 2.04 g of the title compound (80% in yield).

Provenance & Evidence