Diisopropylethylamine → tert-Butyl 3-bromobenzylcarbamate

HRID 1985295Notes

Reaction equation

HRID 1985295 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C(N(CC)C(C)C)(C)C.[C:20](OC([O-])=O)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>ClCCl.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27249803-Bromobenzylamine hydrochlorideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 11033439tert-Butyl 3-bromobenzylcarbamateYield 92.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

26.25 g of 3-Bromobenzylamine hydrochloride was suspended in 250 ml of dichloromethane, and the mixture was cooled to 0° C. 33.5 g of N,N-diisopropylethylamine and 28.3 g of t-butyl dicarbonate were added. After stirring was continued at room temperature overnight, the reaction mixture was diluted with ethyl acetate. The solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off, to give 31.28 g of the title compound.

Workup

  1. washThe solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-11c67f929be84d9ba543fb81859807bc
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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