Hydrochloric Acid → (S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-one

Temperature

65 °C

To a solution of [(S)-1-(4-bromophenyl)-ethyl]-[2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethyl]-amine (6.5 g, 19 mmol) in MeOH (60 mL) was added concentrated aqueous HCl (60 mL). The mixture was stirred at 65° C. till the reaction was finished. The mixture was cooled to 0° C., and the pH of the mixture was adjusted to 7 by adding saturated aqueous NaHCO3. The mixture was concentrated, and the residue was extracted with EtOAc (3×100 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 1-[(S)-1-(4-bromophenyl)-ethylamino]-4-methyl-pentan-3-one (5.5 g, 97%), which was used for the next step without further purification. 1H NMR (CDCl3): δ 1.07 (d, J=6.8 Hz, 6H), 1.29 (d, J=6.4 Hz, 3H), 1.89 (br, 1H), 2.54-2.62 (m, 4H), 2.66-2.69 (m, 1H), 3.68-3.72 (m, 1H), 7.18-7.20 (m, 2H), 7.41-7.44 (m, 2H).

1. temperatureThe mixture was cooled to 0° C.
2. concentrationThe mixture was concentrated
3. extractionthe residue was extracted with EtOAc (3×100 mL)
4. washThe organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-4ec4980cecfc41b9a6044b6ac744f35b

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846668B2