Potassium Carbonate → 1-(2-Butynyl)-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid, ethyl ester

HRID 278338Notes

Reaction equation

HRID 278338 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:28][C:29]#[C:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:28]([N:9]1[CH2:8][CH2:7][C:6]([CH2:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:20][CH:21]=2)(=[O:15])=[O:14])([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1)[C:29]#[C:30][CH3:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 22626999HCID 22626999, compound

Product 1

HCID 867578821-(2-Butynyl)-4-[[[4-(2-butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid, ethyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[[[4-(2-Butynyloxy)phenyl]sulfonyl]methyl]-4-piperidinecarboxylic acid ethyl ester (0.208 g,0.5 mmol), 1-bromo-2-butyne (0.044 ml, 0.53 mmol) and K2CO3 (0.138 g, 1.0 mmol)in 5.0 mL of DMF was stirred at room temperature for 6 h. The reaction was diluted with EtOAc and washed with H2O, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc:hexanes (1:1) to provide 0.183 g (85%) of the desired product as a pale yellow gum. Electrospray Mass Spec: 432.2 (M+H)+

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with EtOAc:hexanes (1:1)

Sources & evidence

ORD record
ord-c00e42b1d59a46b189124ab28f3dca88
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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