Potassium Carbonate → HCID 86689033, compound

HRID 388425

Reaction equation

HRID 388425 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH:15]1([NH2:19])[CH2:18][CH2:17][CH2:16]1>C1COCC1>[CH:15]1([NH:19][CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH3:8])=[O:6])[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75645CyclobutylamineHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Product 1

HCID 86689033HCID 86689033, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-methyl 4-bromobut-2-enoate (5.37 g, 30 mmol) in THF (60 mL) was added potassium carbonate (8.34 g, 60 mmol), followed by cyclobutanamine (2.13 g, 30 mmol, in 30 mL THF) under N2 atmosphere. The resulting reaction mixture was stirred at RT overnight. Excess potassium carbonate was removed by filtration and the filtrate was diluted with EA and water. The organic layer was separated and the aqueous later was extracted with EA. The combined organic phase was dried over Na2SO4. Solvent was removed in vacuum and the crude mixture was purified by flash chromatography (0-5% DCM/MeOH) to provide (E)-methyl 4-(cyclobutylamino)but-2-enoate (19) (1.7 g, 33%) as an oil. LC-MS (ESI): m/z (M+1), 170.2.

Workup

  1. customThe resulting reaction mixture
  2. customExcess potassium carbonate was removed by filtration
  3. additionthe filtrate was diluted with EA and water
  4. customThe organic layer was separated
  5. extractionthe aqueous later was extracted with EA
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. customSolvent was removed in vacuum
  8. customthe crude mixture was purified by flash chromatography (0-5% DCM/MeOH)

Sources & evidence

ORD record
ord-86e2bcdc26d742df83851a1f583167be
Source dataset
uspto-grants-2013_02
Patent number
US08377946B1

Linked notes

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