Acetic Acid → Benzyl 2-(N-(2-bromophenylmethyl)amino)acetate

HRID 1057475Notes

Reaction equation

HRID 1057475 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:20][CH2:19][C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 811292-BromobenzaldehydeHCID 409140Benzyl glycinateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18671460Benzyl 2-(N-(2-bromophenylmethyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-bromobenzaldehyde in dichloromethane (0.2 M) was added glycine benzyl ester (1.2 eq), sodium triacetoxyborohydride (2 eq) and acetic acid (4 eq). After stirring overnight, the solution was washed with 10% sodium carbonate, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (silica; 30%-40% EtOAc/Hexanes) to afford a pale yellow oil. EI-MS m/z 334, 336 (M+H)+

Workup

  1. washthe solution was washed with 10% sodium carbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica; 30%-40% EtOAc/Hexanes)
  6. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-c5329fa3d20c441db171d53df32ff872
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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