Triethylamine → Tert-butyl 2-(cyclobutylamino)acetate

HRID 127614Notes

Reaction equation

HRID 127614 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH:10]1([NH2:14])[CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>>[C:6]([O:5][C:3](=[O:4])[CH2:2][NH:14][CH:10]1[CH2:13][CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 75645CyclobutylamineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 20285462Tert-butyl 2-(cyclobutylamino)acetateYield 67.2%

Procedure

An ethanolic solution of t-butyl bromoacetate (39 g, 0.2 mol) was added dropwise to a stirred chilled ethanolic solution containing cyclobutyl amine (28.4 g, 0.4 mol) and triethylamine (25.3 g, 0.25 mol). After stirring overnight at room temperature, the reaction mixture was concentrated and the residue redissolved in methylene chloride (300 ml). This solution was washed with water (3×500 ml), dried over MgSO4, filtered, and evaporated to dryness, yielding 24.9 g (67%) of the desired product as a light brown oil.

Workup

  1. temperaturechilled ethanolic solution
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe residue redissolved in methylene chloride (300 ml)
  4. washThis solution was washed with water (3×500 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a763cbe104794b3dae93b8f44f1c68ab
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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