Sodium Hydroxide → tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate

HRID 2059882Notes

Reaction equation

HRID 2059882 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][OH:22])(=[O:14])=[O:13])=[C:7]([CH3:23])[CH:6]=1.[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH3:23])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][O:22][CH2:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:32])(=[O:13])=[O:14])=[C:9]([CH3:11])[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 43574491[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanol

Product 1

HCID 57916265tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetateYield 64%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

tetra-n-Butylammonium chloride (0.33 eq) and sodium hydroxide solution (5 ml/mmol, 35%) were added to a cooled solution of (1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (1 eq) in toluene (5 ml/mmol) at 0° C. tert-Butylbromoacetate (1.5 eq) was then slowly added dropwise at 0° C. After stirring the mixture at room temperature for 90 min the phases were separated, the organic phase was washed with water to a neutral pH, dried over sodium sulfate and concentrated to small volume under vacuum. The crude product was used in the next stage with no further purification. Yield: 64%

Workup

  1. additionwas then slowly added dropwise at 0° C
  2. customwere separated
  3. washthe organic phase was washed with water to a neutral pH
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to small volume under vacuum
  6. customThe crude product was used in the next stage with no further purification

Sources & evidence

ORD record
ord-80a8aee371fd47a5960549e8b86101bb
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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