Cyclopropylamine → Tert-butyl 2-(cyclopropylamino)acetate

HRID 127611Notes

Reaction equation

HRID 127611 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(O)C>[C:15]([O:14][C:12](=[O:13])[CH2:11][NH:4][CH:1]1[CH2:3][CH2:2]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 79177tert-Butyl bromoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 20285435Tert-butyl 2-(cyclopropylamino)acetateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopropylamine (19.5 g, 0.342 mol) was placed in a pressure bottle and ethanol (100 ml.) was added. The resulting solution was cooled in an ice bath and sodium bicarbonate (8.5 g, 0.101 mol) and t-butyl bromoacetate (15.5 g, 0.0795 mol) was added. The flask was stoppered and the contents of the flask were stirred for 30 minutes with external cooling (ice bath) and then at room temperature overnight. Most of the solvent was removed on a rotary evaporator and water was added to the residue. The product was extracted several times with chloroform. The combined chloroform extract was washed with water, dried over sodium sulfate, filtered and evaporated to yield the product as a pale yellow oil (12.5 g, 92%).

Workup

  1. additionwas added
  2. temperatureThe resulting solution was cooled in an ice bath
  3. temperaturewith external cooling (ice bath)
  4. customat room temperature
  5. customovernight
  6. customMost of the solvent was removed on a rotary evaporator and water
  7. additionwas added to the residue
  8. extractionThe product was extracted several times with chloroform
  9. extractionThe combined chloroform extract
  10. washwas washed with water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-380632d135424ce19446f81f16bac5f2
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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