tert-Butyl bromoacetate → HCID 68780476, compound

HRID 2090824Notes

Reaction equation

HRID 2090824 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Br:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([S:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]2[CH2:27][OH:28])(=[O:20])=[O:19])=[C:13]([CH3:29])[CH:12]=1.CCOC(C)=O.CCCCCC>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([S:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]2[CH2:27][O:28][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])(=[O:19])=[O:20])=[C:13]([CH3:29])[CH:12]=1

Participants

6

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 21226206Ethyl acetate hexaneHCID 67454827HCID 67454827, compound

Product 1

HCID 68780476HCID 68780476, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

180 ml of 50% sodium hydroxy solution and 180 ml of tert-butyl bromoacetate were added to a solution of 18 g of (1-(4-bromo-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol, and stirring was carried for 10 minutes. 1.815 g of tetra-n-butylammonium hydrogen sulfate were then added, and stirring was carried out for a further 45 minutes at room temperature. The progress of the reaction was monitored by thin-layer chromatography (20% EtOAc/hexane). When the reaction was complete, 400 ml of ethyl acetate were added, and the phases were separated. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica; 5% EtOAc/hexane). tert-butyl 2-((1-(4-bromo-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate was obtained in a yield of 78.2% (18 g).

Workup

  1. stirringstirring
  2. waitwas carried out for a further 45 minutes at room temperature
  3. customthe phases were separated
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica; 5% EtOAc/hexane)

Sources & evidence

ORD record
ord-72c73fea62644d758b4a51d906e72849
Source dataset
uspto-grants-2013_05
Patent number
US08435978B2

Reaction notes

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