Sodium borohydride → 2-Amino-2-phenylpropan-1-ol

The product of Example 96G (0.58 g, 3.2 mmol) and sodium borohydride (0.12 g, 3.2 mmol) in 75% aqueous EtOH (7.6 mL) were refluxed for 1.5 hours. The reaction mixture was concentrated and the residue was diluted with water (15 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was washed with water (2×10 mL) and brine, dried over MgSO4, concentrated to give the title compound as colorless viscous oil, which later crystallized (0.27 g, 55%). 1H-NMR (300 MHz, CDCl3) δ ppm: 1.46 (s, 3H), 1.86 (br-s, 2H), 3.59 (d, J=10.7 Hz, 1H), 3.65 (d, J=10.7 Hz, 1H), 7.22-7.30 (m, 1H), 7.31-7.41 (m, 2H), 7.41-7.49 (m, 2H). MS ESI+ m/z: 152 (M+H).

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with water (15 mL)
3. extractionextracted with ethyl acetate (2×25 mL)
4. washThe organic layer was washed with water (2×10 mL) and brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD record

ord-56516e0c48cb48e3b900c67a2b908b14

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236950B2