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

HRID 332606Notes

Reaction equation

HRID 332606 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-f2ae2cc1aee245d2903123090f5add71
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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