Pyridine → N-[(1R)-1-(4-bromophenyl)ethyl]acetamide

Temperature

25 °C

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.52 g, 2.59 mmol) in anhydrous CH2Cl2 (5 mL) under argon were added acetic anhydride (0.37 mL, 3.89 mmol) and Pyridine (0.31 mL, 3.89 mmol). The resulting solution was stirred at 25° C. for 3 hrs. The reaction mixture was quenched with saturated 1N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (80% EtOAc in hexanes) to give the product (0.62 g, 100%) as a white solid. 1H NMR (CDCl3) δ: 1.46 (d, J=7.0 Hz, 3H), 1.99 (s, 3H), 5.03-5.12 (m, 1H), 5.68 (brs, 1H), 7.18 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H). ESIMS (MNa+): 264.

1. customThe reaction mixture was quenched with saturated 1N HCl
2. extractionextracted with EtOAc (30 mL)
3. washThe organic phase was washed with brine (50 mL)
4. dry with materialdried over Na2SO4
5. customevaporated
6. customThe residue was purified by flash column chromatography (80% EtOAc in hexanes)

ORD record

ord-aff036d6eba140e79129cd39e1aa9468

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2