Methanol → 2-Amino-4,4,4-trifluorobutan-1-ol

0.32 ml (0.65 mmol) of lithium borohydride (2 M in THF) were initially charged in 0.5 ml of dry THF, 0.16 ml (1.28 mmol) of chlorotrimethylsilane were added at RT and the mixture was stirred at RT for 5 min. 50 mg (0.26 mmol) of 2-amino-4,4,4-trifluorobutanoic acid hydrochloride (1:1) were then added a little at a time, and the reaction mixture was stirred at RT overnight. 0.5 ml of methanol was added, and the mixture was then concentrated. 0.6 ml of a 20% strength solution of potassium hydroxide was then added to the residue, and the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 33 mg of the target compound (88% of theory).

1. stirringthe reaction mixture was stirred at RT overnight
2. concentrationthe mixture was then concentrated
3. addition0.6 ml of a 20% strength solution of potassium hydroxide was then added to the residue
4. extractionthe mixture was extracted three times with dichloromethane
5. dry with materialThe combined organic phases were dried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-99d8d13ecf9c4f85839342cd4100d489

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778964B2