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

Temperature

50 °C

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+].

1. waitThe mixture was left
2. temperatureto cool
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was re-dissolved in DCM (25 mL)
5. additiontreated with MeOH (2 mL)
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in MeOH (25 mL)
8. concentrationre-concentrated in vacuo
9. customThe residue was purified by FCC

ORD record

ord-b0a2d829cac24efea6557578a03c305d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181242B2