Hydrochloric Acid → (S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]2([CH:18]([CH3:20])[CH3:19])OCC[O:14]2)[CH3:9])=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13](=[O:14])[CH:18]([CH3:20])[CH3:19])[CH3:9])=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
To a solution of (S)-1-(4-bromophenyl)-N-(2-(2-isopropyl-1,3-dioxolan-2-yl)ethyl)ethanamine (6.5 g, 19 mmol) in MeOH (60 mL) was added conc 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 the satd aq 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 (S)-1-(1-(4-bromophenyl)ethylamino)-4-methylpentan-3-one (5.5 g, 97% yield), 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).
Workup
- temperatureThe mixture was cooled to 0° C.
- concentrationThe mixture was concentrated
- extractionthe residue was extracted with EtOAc (3×100 mL)
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c339ca4922084bf29a3f3e5bad57f53f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575157B2
Reaction notes
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