5-Amino-2-fluorophenylacetic acid → 2-(5-Amino-2-fluoro-phenyl)-ethanol

Participants

Reaction Conditions

Reaction Steps

Borane-THF complex (1M, 11.8 mL, 11.8 mmol) was added to a solution of (5-amino-2-fluoro-phenyl)-acetic acid (1.00 g, 5.91 mmol) in dry THF (10 mL), under argon, over 20 min. Once the effervescence had ceased, the reaction mixture was heated to 50° C. for 2 h. The mixture was left to cool and then concentrated in vacuo. The residue was re-dissolved in DCM (25 mL) and treated with MeOH (2 mL). The mixture was stirred vigorously and then concentrated in vacuo. The residue was dissolved in MeOH (25 mL) and re-concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to afford the title compound (0.54 g, 59%). LCMS (Method 3): Rt: 0.41 min, m/z 156 [MH+].

Provenance & Evidence