Tetrahydrofuran → Ethyl acetate methanol ammonium hydroxide

To 3-[3-cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (29 mg, 0.054 mmol) in THF (2 mL) at 0° C. under argon was added lithium aluminum hydride (14 mg) in one portion. The resulting mixture was allowed to stir at ambient temperature for 7 h before quenching with water (2 mL) and 1.0 M sodium hydroxide (1 mL). The stirring was continued for 30 min. The mixture was further diluted with brine (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with NH4OH:MeOH:EtOAc (5:10:85) afforded the product (7 mg, 24%).

1. custombefore quenching with water (2 mL) and 1.0 M sodium hydroxide (1 mL)
2. waitThe stirring was continued for 30 min
3. additionThe mixture was further diluted with brine (50 mL)
4. extractionextracted with dichloromethane (50 mL×3)
5. dry with materialThe combined organic layers were dried with sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-d5d1ab426d724759bf3be23219e37e1e

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06251921B1