Potassium tert-butoxide → HCID 68432290, compound

HRID 1867426Notes

Reaction equation

HRID 1867426 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH2:9][N:10]([C:24](=[O:27])[CH:25]=[CH2:26])[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:7]1[CH2:26][CH2:25][C:24](=[O:27])[N:10]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH2:9][CH2:8]1)=[O:28])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 68433175HCID 68433175, compound

Product 1

HCID 68432290HCID 68432290, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of {2-[Acryloyl-(1-benzyl-piperidin-4-yl)-amino]-ethyl}-carbamic acid tert-butyl ester (4.6 g, 12 mmol) in DMF (40 ml) was added potassium tert-butoxide (0.1 g, 1 mmol) and the reaction stirred for 2 h after which time it was concentrated, the residue dissolved in CH2Cl2, washed with saturated NaHCO3, dried (Na2SO4), and concentrated. The product was isolated by flash column chromatography (CH2Cl2:MeOH 9:1) to afford the title compound (3.5 g, 75%) as a white solid. MS: 388.3 (MH+)

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product was isolated by flash column chromatography (CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-2cd43fd1fc1a4136b2a06388cba79238
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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