Hydrochloric Acid → 3,3,3-Trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine

Participants

Reaction Conditions

Reaction Steps

A solution of LiBH4 (2M THF, 19.66 mL, 39.33 mmol) was added to a solution of methyl 4,4,4,4′,4′,4′-hexafluoro-dl-valinate (2.35 g, 9.83 mmol) in THF (80 mL) at 0° C. The reaction was allowed to warm to 25° C. After 19 h, the reaction was cooled to 0° C. and 2M HCl was added to the reaction mixture very carefully until pH<2. The organic solvent was removed in vacuo and the aqueous layer was neutralized with sat NaHCO3 until pH=7. The aqueous layer was extracted with EtOAc (2×50 mL) and the organic extracts were dried over Na2SO4 and concentrated to provide 3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propyl amine as a yellow oil (1.7 g, 82% yield). The crude oil was of sufficient purity to utilize in the subsequent reaction. Mass Spectrum (−ESI): 210 [M−H]−.

Provenance & Evidence