Ethyl bromoacetate → HCID 69891019, compound

HRID 1837966Notes

Reaction equation

HRID 1837966 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH2:11])[CH3:10])=[CH:5][CH:4]=1.CCN(CC)CC.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 793467(S)-1-(4-Methoxyphenyl)ethylamine

Product 1

HCID 69891019HCID 69891019, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of (S)-(−)-1-(4-methoxyphenyl)ethylamine (25 g, 165 mmol) and Et3N (46 mL, 330 mmol) in THF (350 mL) was added a solution of ethyl bromoacetate (27.5 mL, 248 mmol) in THF (50 mL) dropwise over 30 min. The reaction mixture was allowed to warm to room temperature, stirred overnight, then diluted with EtOAc and washed with water and a saturated NaCl solution. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give ethyl 2-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetate (40 g, 100%) as a colorless oil: TLC (40% EtOAc/hex) Rf 0.4; 1H NMR (CDCl3) δ 1.25 (t, J=7.2 Hz, 3H), 1.37 (d, J=6.6 Hz, 3H), 2.03 (br s, 1H), 3.21 (d, J=17.6 Hz, 1H), 3.29 (d, J=17.6 Hz, 1H),), 3.76 (q, J=6.6 Hz, 1H), 3.81 (s, 3H), 4.16 (q, J=7.2 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 7.23 (d, J=8.7 Hz, 2H); 13C NMR (CDCl3) δ 14.1, 24.2, 48.8, 55.2, 57.0, 60.6, 113.8, 127.8, 136.6, 158.7, 172.6; HPLC ES-MS m/z (rel abundance) 238 (MH+, 100%).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4137447fdcc49f0bbccc7b7a65adc24
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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