Hydrochloric Acid → HCID 86762187, compound

Participants

Reaction Conditions

Reaction Steps

3-Benzo[b]thiophen-3-yl-3-hydroxy-propionitrile (1.2 g, 5.90 mmol) was slowly treated with a solution of borane-tetrahydrofuran complex (13 mL, 12.98 mmol, 1M in tetrahydrofuran) at 0° C. After bubbling ceased, the reaction mixture was heated to 75° C. for 2 hours and 6.0 eq of additional borane was added to drive the reaction to completion. The reaction mixture was concentrated. The white solid obtained was treated with methanol (14 mL), followed by hydrogen chloride (2M in diethyl ether, 43 mL). The resulting mixture was heated to reflux for 2 hours, allowed to cool to ambient temperature and then concentrated at reduced pressure. To the residue was added aqueous hydrochloric acid (10 mL, 1 N) followed by diethyl ether (20 mL). The aqueous layers were separated and concentrated at reduced pressure to give the product as a yellow solid (840 mg, 58%).

Provenance & Evidence