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

12.9 ml of 2 M 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. 2.0 g of rac-2-amino-4,4,4-trifluorobutanoic acid hydrochloride (10.3 mmol, 1 equivalent) were then added a little at a time, and the mixture was stirred at RT overnight. 20.4 ml of methanol were then added dropwise, and after the addition had ended the mixture was concentrated. 12 ml of a 20% strength aqueous potassium hydroxide solution were added to the residue, and the mixture was extracted three times with dichloromethane. The combined organic solutions were dried over sodium sulphate, filtered and concentrated. This gave 1.58 g (96% of theory; purity 90%) of the title compound.

1. stirringthe mixture was stirred at RT overnight
2. additionafter the addition
3. concentrationwas concentrated
4. addition12 ml of a 20% strength aqueous potassium hydroxide solution were added to the residue
5. extractionthe mixture was extracted three times with dichloromethane
6. dry with materialThe combined organic solutions were dried over sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-cc7fa6f3276c46feb2d96d3b95084fc5

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126998B2