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

0.32 ml of lithium borohydride (2 M in THF, 0.65 mmol, 2.5 equivalents) were initially charged in 0.5 ml of abs. THF, 0.16 ml of chlorotrimethylsilane (1.28 mmol, 5 equivalents) were added at RT and the mixture was stirred at RT for 5 min. 50 mg of 2-amino-4,4,4-trifluorobutanoic acid hydrochloride (0.26 mmol, 1 equivalent) 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, 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 title 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
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-1d29880ad4d4428fa5e3d163a6fee260

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126998B2