Hydrochloric Acid → HCID 11531386, compound

Participants

Reaction Steps

To a suspension of lithium borohydride (4.11 g) in tetrahydrofuran (50 mL) was added a solution of 1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carboxylic acid ethyl ester (16.6 g) in a mixture of tertrahydrofuran (80 mL) and methanol (7.7 mL) in an ice-cooling bath. The mixture was stirred at room temperature for 2 hours. After cooling with an ice-cooling bath, water was added and the mixture was poured slowly into a 3M HCl aqueous solution. The solution was made to alkaline (pH=8) with 4 M NaOH aqueous solution to give a solid. The solid was collected by filtration and washed with water and diethylether. The solid was recrystallized from a mixture of ethanol and ethyl acetate to give {1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}methanol (9.1 g).

Provenance & Evidence