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

HRID 529209Notes

Reaction equation

HRID 529209 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., 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-1084415a61834095a6a4dafcc7357bb9
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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