2-Chlorobenzylamine → N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide

HRID 655943Notes

Reaction equation

HRID 655943 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4](OC)=[O:5].[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH:14][C:4](=[O:5])[C:3]([CH3:9])([CH3:8])[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 666482-ChlorobenzylamineHCID 84152Methyl 3-hydroxypivalateHCID 16682925Trimethylaluminum

Product 1

HCID 59778447N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamideYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1 g, 7.31 mmol) and 2-chlorobenzylamine (1 mL, 8.75 mmol, 1.2 equiv.) in toluene (7 mL) was added trimethylaluminum (2 M in hexane, 5.4 mL, 10.8 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.5 g, 85%), which was used without further purification. LRMS (M+H+) m/z 242.1.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-afd96c4c71a64cd48db01043faa14c79
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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