Hydrochloric Acid → HCID 86762187, compound

Temperature

75 °C

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%).

1. customAfter bubbling
2. customthe reaction to completion
3. concentrationThe reaction mixture was concentrated
4. customThe white solid obtained
5. temperatureThe resulting mixture was heated
6. temperatureto reflux for 2 hours
7. temperatureto cool to ambient temperature
8. concentrationconcentrated at reduced pressure
9. additionTo the residue was added aqueous hydrochloric acid (10 mL, 1 N)
10. customThe aqueous layers were separated
11. concentrationconcentrated at reduced pressure

ORD record

ord-7ffa74a75d174d6ca566d863b1cdfbaa

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609849B1