Ethyl oxoacetate → 37662-06-9

HRID 1436497Notes

Reaction equation

HRID 1436497 reaction equation
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=O>ClCCl>[CH2:15]([O:14][C:10](=[O:13])[CH:11]=[N:9][C@H:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:1])[CH3:16]

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 758181-Phenethylamine, (-)-

Product 1

HCID 1146979737662-06-9Yield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Treat a solution of neat (S)-α-methylbenzylamine (7.5 mL, 59 mmol) in dichloromethane (300 mL) at 0° C. with ethyl glyoxalate solution (50% in toluene, 11.5 mL). Add 4Å molecular sieves (20 g) to the above solution. Stir the reaction mixture at 0° C. for 2 h. Filter the solids off, concentrate and purify (silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes) to give the title compound (11.1 g, 97%)

Workup

  1. additionAdd 4Å molecular sieves (20 g) to the above solution
  2. filtrationFilter the solids off,
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-e346c3eefe194841a0276718261f74ea
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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