Toluene → HCID 19067143, compound

HRID 481772Notes

Reaction equation

HRID 481772 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([O:15][C:16]([N:18]1[CH:23]([CH3:24])[CH2:22][CH:21]([OH:25])[CH2:20][CH:19]1[CH3:26])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[OH-].[Na+]>S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:8]([O:15][C:16]([N:18]1[CH:19]([CH3:26])[CH2:20][CH:21]([O:25][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:22][CH:23]1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 19067156HCID 19067156, compound

Product 1

HCID 19067143HCID 19067143, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 962WaterSolvent

Procedure

To 10 ml of toluene was dissolved 1.91 g of N-benzyloxycarbonyl-2,6-dimethyl-4-hydroxypiperidine, and to this solution were added 1.70 g of tert-butyl bromoacetate, 0.08 g of tetrabutylammonium sulfate and 1 ml of water, and then aqueous solution of sodium hydroxide in an ice bath. The solution was stirred overnight at room temperature, washed with water and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. From the fractions eluted with chloroform-methanol (100:1 v/v) was obtained 1.11 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-2,6-dimethylpiperidine, which was an oily product (yield: 41%).

Workup

  1. washwashed with water and saturated aqueous solution of sodium chloride
  2. dry with materialdried with anhydrous sodium sulfate
  3. customAfter separating the desiccant
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography
  7. washFrom the fractions eluted with chloroform-methanol (100:1 v/v)

Sources & evidence

ORD record
ord-569f6bfbc23e433a9a89971e97992e22
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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