1-Phenethylamine, (+)- → 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propyl acetate

HRID 515460Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)[CH2:14][O:15][C:16](=[O:18])[CH3:17])(=O)=O)=CC=1.[C:26]1([C@H:32]([NH2:34])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[C:16]([O:15][CH2:14][CH:13]([C:19]1[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=1)[CH2:12][NH:34][C@@H:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:33])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (+)-3-acetoxy-2-(4-bromophenyl)propyl 4-methylbenzene-sulfonate (8.00 g, 18.7 mmol) in N,N-dimethylformamide (94.0 ml) was added (R)-(+)-1-phenylethylamine(11.3 g, 93.2 mmol) at room temperature. The mixture was stirred at 120° C. for 7 hours and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=7/3) to afford diastereopure 3-((R)-1-phenylethylamino)-2-(4-bromophenyl)propyl acetate as pale yellow oil (2.85 g, 40%).

Workup

concentrationconcentrated in vacuo
customThe residue was partitioned between water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=7/3)

Sources & evidence

ORD record: ord-b8fa535c556c475e929aa647f6c86e06
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108957B2

Reaction notes

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