Allylamine → Tert-butyl 2-[(prop-2-en-1-yl)amino]acetate

HRID 517337Notes

Reaction equation

HRID 517337 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[C:5]([O:9][C:10](=[O:13])[CH2:11]Br)([CH3:8])([CH3:7])[CH3:6]>ClCCl>[C:5]([O:9][C:10](=[O:13])[CH2:11][NH:4][CH2:1][CH:2]=[CH2:3])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Conditions

Temperature
0 °C

Procedure

Allylamine (10 mL, 0.13 mol) was cooled to 0° C., and a solution of bromoacetic acid tert-butyl ester (1.0 mL, 6.7 mmol) in dichloromethane (10 mL) was slowly added. After stirring at 0° C. for 3 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in diethyl ether, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The obtained solution was concentrated under reduced pressure to give the title compound as a yellow liquid (1.15 g, 6.7 mmol, 99%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in diethyl ether
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-471c952cd846495092a22e16792652ce
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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