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

Participants

Reaction Steps

To a suspension of LiBH4 (62.7 mg, 2.88 mmol) in THF (1.5 mL) was added TMSCl (728 μL, 5.76 mmol) and the reaction mixture was stirred at room temperature for 15 min, followed by the addition of 2-amino-4,4,4-trifluorobutanoic acid (226 mg, 1.44 mmol). The reaction mixture was stirred at room temperature for 18 h, and quenched by careful addition of MeOH. The solvents were removed by reduced pressure, and to the residue was added H2O (2.08 mL). The resulting aqueous portion was made basic by adding 2 N NaOH. The mixture was extracted with CH2Cl2 three times. The combined organic portions were dried over MgSO4, filtered and concentrated to give 2-amino-4,4,4-trifluorobutan-1-ol as a colorless oil (110 mg, 53% yield). NMR: 400 MHz 1H (CDCl3) 3.61 ppm, 1 H, dd, J=10.61, 4.04 Hz; 3.42 ppm, 1 H, m; 3.28 ppm, 1 H, m; 2.29 ppm, 1 H, m; 2.12 ppm, 1 H, m.

Provenance & Evidence