Water → HCID 19067200, compound

HRID 481776Notes

Reaction equation

HRID 481776 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH:13]([CH3:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]([CH3:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 19067136HCID 19067136, compound

Product 1

HCID 19067200HCID 19067200, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 1140TolueneSolvent

Procedure

2.53 g of N-benzyloxycarbonyl-4-hydroxy-3-methyl-piperidine was dissolved in 20 ml of toluene, and to this solution was added 2.96 g of tert-butyl bromoacetate, 0.1 g of tetrabutylammonium sulfate and 1 ml of water. Aqueous solution (10.1 g) of sodium hydroxide was added dropwise to this solution in an ice bath, and the solution was stirred overnight at room temperature. The resulting solution was washed with water and saturated 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 (100:3 v/v) was obtained 1.59 g of N-benzyloxycarbonyl-4-tert-butoxycarbonylmethyloxy-3-methylpiperidine, which was an oily product (yield: 44%).

Workup

  1. washThe resulting solution was washed with water and saturated 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 (100:3 v/v)

Sources & evidence

ORD record
ord-8fb3fc5bc79849d8930894776031fa26
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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