Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 21460406, compound

HRID 1941216Notes

Reaction equation

HRID 1941216 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].CN1CCCC1=O>O>[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 13387N-methyl-2-pyrrolidoneHCID 5338682-(Benzyloxy)ethanamine

Product 1

HCID 21460406HCID 21460406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-benzyloxyethylamine (50 g), ethyl 2-bromo-2-methylpropionate (97.5 g) and N-methyl-2-pyrrolidone (1 l) was heated at 100° C. for 7 h. The mixture was cooled to room temperature, water was added and the resulting mixture was extracted with ethyl acetate (2×500 ml). The combined organic phases were washed with water (4×500 ml) and brine (2×500 ml), dried (Na2SO4) and the solvents were evaporated in vacuo. Purification of the remaining oil by column chromatography on silica gel (ethyl acetat containing 4% triethylamine) gave ethyl 2-(2-benzyloxyethylamino)-2-methylpropionate as an oil: 30 g

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (2×500 ml)
  3. washThe combined organic phases were washed with water (4×500 ml) and brine (2×500 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvents were evaporated in vacuo
  6. customPurification of the remaining oil by column chromatography on silica gel (ethyl acetat containing 4% triethylamine)

Sources & evidence

ORD record
ord-11a1545f69c248498a0586a8cda7c027
Source dataset
uspto-grants-1997_12
Patent number
US05703087

Reaction notes

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