Aluminium lithium hydride → HCID 86594857, compound

A solution of (R)-(4,4,4-trifluoro-3-hydroxybutyl)carbamic acid tert-butyl ester (3.17 g, 13.0 mmol) in THF (130 mL) was treated with lithium aluminium hydride (1.97 g, 52.0 mmol) at ambient temperature, followed by refluxing for 2 h. Heating was stopped, additional lithium aluminium hydride (0.490 g, 12.9 mmol) was added, and refluxing was continued for 1 h. The mixture was cooled to 0–5° C. and carefully quenched with excess sodium sulfate decahydrate. Additional THF and diethyl ether were added to aid stirring. The mixture was filtered through Celite™ and the filtrate was evaporated to a white wax. The wax was purified by trituration with 9:1 hexane/diethyl ether (v/v) to give the product as a white solid (1.56 g, 76%).

1. temperatureby refluxing for 2 h
2. temperatureHeating
3. temperaturerefluxing
4. temperatureThe mixture was cooled to 0–5° C.
5. customcarefully quenched with excess sodium sulfate decahydrate
6. additionAdditional THF and diethyl ether were added to aid
7. filtrationThe mixture was filtered through Celite™
8. customthe filtrate was evaporated to a white wax
9. customThe wax was purified by trituration with 9:1 hexane/diethyl ether (v/v)

ORD record

ord-5b472ed0671f4ecea4155fc09de2972d

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119109B2