Chlorotrimethylsilane → HCID 86594496, compound

Temperature

25 °C

To a solution of LiBH4 (0.35 mL, 0.71 mmol) in THF (5 mL) at 0° C. was added chlorotrimethylsilane (0.112 mL, 0.885 mmol). The reaction mixture was warmed to 25° C. and, after 30 min, added dropwise to a 0° C. suspension of crude 5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-L-norvaline hydrochloride salt (0.045 g, 0.177 mmol) in THF (1 mL). The mixture was warmed to 25° C. and, after 21 h, quenched with MeOH. The volatiles were removed in vacuo to give a residue, which was dissolved in 1N aqueous NaOH (5 mL) and extracted with CH2Cl2 (4×10 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain (2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentan-1-ol as a crude light yellow oil (0.046 g, 100%). The crude amino alcohol was used in the next step without further purification. Mass Spectrum (+ESI): 240 (M+H)+.

1. additionadded dropwise to a 0° C.
2. temperatureThe mixture was warmed to 25° C. and, after 21 h
3. customquenched with MeOH
4. customThe volatiles were removed in vacuo
5. customto give a residue, which
6. extractionextracted with CH2Cl2 (4×10 mL)
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-e36d2c4daea249e59cd09bd204a330a7

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858658B2