Hydrochloric Acid → HCID 58856349, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-amino-2-benzyl-3-fluoropropanoic acid (50 mg, 0.25 mmol) (for synthesis see EP 0 040 150 A1) in 2.5 mL THF, cooled to 0° C., was added borane-tetrahydrofuran complex (1M in THF, 0.75 mL, 0.75 mmol) dropwise. The reaction was stirred at rt overnight, quenched with MeOH and concentrated. Hydrochloric acid (1M, 7.5 mL, 7.5 mmol) was added, the mixture was heated to 45° C. for 1 h and concentrated. The reaction was made basic with saturated NaHCO3 and exacted with CHCl3. Drying and solvent evaporation gave 2-amino-2-(fluoromethyl)-3-phenylpropan-1-ol. 1H NMR (400 MHz, CDCl3) δ 7.35-7.21 (m, 5H), 4.30-4.11 (two q, ABX system, J=47.4 Hz, J=20.8 Hz, J=9.0 Hz, 2H), 3.49 (m, 2H), 2.76 (m, 2H).

Provenance & Evidence