Potassium Carbonate → HCID 58724108, compound

HRID 2356217Notes

Reaction equation

HRID 2356217 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:15]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:22]([O:21][C:19]([C:15]1([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:18][CH2:17][CH2:16]1)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 97595Ethyl 1-bromocyclobutanecarboxylateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 58724108HCID 58724108, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

Tert-Butyl piperazine-1-carboxylate (0.50 g, 2.7 mmol) and ethyl 1-bromocyclobutanecarboxylate (0.52 ml, 3.2 mmol) were dissolved in DMF (5 ml). Potassium carbonate was added, and the mixture was heated to 85° C. for 24 h. The mixture was diluted with brine and then extracted twice with EtOAc. Combined organic layers were washed once with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, gradient, 45-55% EtOAc/hexanes) to give tert-butyl 4-(1-(ethoxycarbonyl)cyclobutyl)piperazine-1-carboxylate as a colorless oil (223 mg, 27%).

Workup

  1. extractionextracted twice with EtOAc
  2. washCombined organic layers were washed once with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (SiO2, gradient, 45-55% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ce5a556f4137400bbc2a93a114a0b339
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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