Allyl bromide → Methyl 2-(allyl(benzyl)amino)acetate

HRID 712388Notes

Reaction equation

HRID 712388 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C=O)C>[CH2:22]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 422659Methyl 2-(benzylamino)acetate

Product 1

HCID 10798914Methyl 2-(allyl(benzyl)amino)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-(benzylamino)acetate (21.30 g, 119.2 mmol, 1.0 eq) in DMF (150 mL) was added anhydrous K2CO3 (8.02 g, 143.02 mmol, 1.2 eq) followed by allyl bromide (12.37 mL, 143.02 mmol, 1.2 eq) at room temperature. The mixture was stirred for 4 h, quenched with water and extracted with EtOAc (100 mL×3). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (20:1 (v/v) PE/EtOAc) to afford the title compound as colorless oil (18.30 g, 70%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ: 3.27 (2H, d, J=6.4 Hz), 3.32 (2H, s), 3.68 (3H, s), 3.78 (2H, s), 5.19 (2H, m), 5.88 (1H, m), 7.23-7.35 (5H, m) ppm.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (100 mL×3)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (20:1 (v/v) PE/EtOAc)

Sources & evidence

ORD record
ord-478313ea32084cbeabf25626260de7fd
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…