Chlorotrimethylsilane → HCID 86594496, compound

Participants

Reaction Conditions

Reaction Steps

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)penta-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)+.

Provenance & Evidence