Water → Tert-butyl 2-(cyclobutylamino)acetate

HRID 1026760Notes

Reaction equation

HRID 1026760 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:1]1([NH:5][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 20285462Tert-butyl 2-(cyclobutylamino)acetateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyclobutylamine (370 mg) was added to an ice-cold suspension of tert-butyl bromoacetate (1.0 g) and potassium carbonate (700 mg) in acetonitrile (20 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, which was then extracted with chloroform. The organic phase was separated out and the solvent was distilled off under reduced pressure to afford tert-butyl N-cyclobutylglycinate (949 mg) as the residue.

Workup

  1. extractionwas then extracted with chloroform
  2. customThe organic phase was separated out
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3cf15e2071f14304aa636c1d04f98d8c
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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