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

12.9 ml of 2 M of lithium borohydride solution in THF (25.8 mmol, 2.5 equivalents) were initially charged in 20 ml of THF, 6.5 ml of chlorotrimethylsilane (51.1 mmol, 5 equivalents) were added and the mixture was stirred at RT for 5 min. Then 2.0 g of rac-2-amino-4,4,4-trifluorobutanoic acid hydrochloride (10.3 mmol, 1 equivalent) were added in portions and the mixture was stirred at room temperature overnight. Then 20.4 ml of methanol were added dropwise and, on completion of addition, the mixture was concentrated. The residue was admixed with 12 ml of a 20% aqueous potassium hydroxide solution and extracted three times with dichloromethane. The combined organic solutions were dried over sodium sulphate, filtered and concentrated. 1.58 g (96% of theory; 90% purity) of the title compound were obtained.

1. stirringthe mixture was stirred at room temperature overnight
2. concentrationthe mixture was concentrated
3. extractionextracted three times with dichloromethane
4. dry with materialThe combined organic solutions were dried over sodium sulphate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-208b4667cd34443eb882545ae298d99a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2