Aluminium lithium hydride → HCID 21928328, compound

A solution of (4,4,4-trifluoro-3-hydroxybutyl)carbamic acid tert-butyl ester (0.55 g, 2.26 mmol) in THF (21 mL) was treated with lithium aluminium hydride (0.321 g, 8.46 mmol) at ambient temperature, followed by refluxing for 3 h. The mixture was cooled to ambient temperature and carefully quenched with excess sodium sulphalte decahydrate. Additional THF and diethyl ether were added to aid stirring. The mixture was filtered through a bed of Celite™ and the filtrate was evaporated to a white solid. The solid was purified by silica gel chromatography, eluting with 10% 2M ammonia in methanol/90% dichloromethane and 20% 2M ammonia in methanol/80% dichloromethane (v/v), to give the product as a white solid (0.218 g, 61%).

1. temperatureby refluxing for 3 h
2. customcarefully quenched with excess sodium sulphalte decahydrate
3. additionAdditional THF and diethyl ether were added to aid
4. filtrationThe mixture was filtered through a bed of Celite™
5. customthe filtrate was evaporated to a white solid
6. customThe solid was purified by silica gel chromatography
7. washeluting with 10% 2M ammonia in methanol/90% dichloromethane and 20% 2M ammonia in methanol/80% dichloromethane (v/v)

ORD record

ord-d033a6d9b2434477892bfc458a9fa467

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119109B2