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 1.0M 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 1.0M 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-45374e004d494593a0270364f1813a86

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06025382