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

A solution of trimethylsilyl chloride (1.38 g, 12.73 mmol) was added to a solution of lithium borohydride (3.2 mL, 2.0 M in THF) and THF (5 mL) at 25° C. After stirring 5 min, 2-amino-4,4,4-trifluoro-butyric acid (0.50 g, 3.18 mmol) was added portionwise over a 5 min period. The reaction was allowed to stir 48 h. The reaction was quenched by cautious addition of MeOH (5 mL) dropwise. The solvent was evaporated and the residue treated with potassium hydroxide (KOH) solution (20%, 6 mL). The aqueous phase was extracted using dichloromethane, 3 times (10 mL each). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration the solvent was evaporated to afford the 2-amino-4,4,4-trifluoro-butan-1-ol as an oil (0.174 g, 38%). This oil was used directly in the next reaction without further purification.

1. stirringto stir 48 h
2. customThe reaction was quenched by cautious addition of MeOH (5 mL) dropwise
3. customThe solvent was evaporated
4. additionthe residue treated with potassium hydroxide (KOH) solution (20%, 6 mL)
5. extractionThe aqueous phase was extracted
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationAfter filtration the solvent
8. customwas evaporated

ORD record

ord-f05b3188e6c5405da193846d7b2effe3

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2