Sodium Hydroxide → HCID 69672744, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Methyl (2S)-tert-butoxy[4-(4-chlorophenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (60 mg, 131 μmol) in tetrahydrofuran (2 mL) and methylated spirit (2 mL) was added an aqueous sodium hydroxide solution (1 M, 790 μL, 790 μmol). The resulting solution was stirred at 60° C. for 3 hours. The volatile solvents were removed in vacuo and the residue diluted with water (10 mL). Dichloromethane (20 mL) was added to the mixture, which was then acidified to pH 5 by the addition of 2 M aqueous hydrochloric acid. The organic layer was separated and washed with water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was recrystallised from 2-propanol and the resulting solid collected by filtration to give the title compound as a white solid, 11.2 mg, in a 19% yield.

Provenance & Evidence