Benzyl Chloride → Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate

HRID 2300161Notes

Reaction equation

HRID 2300161 reaction equation
[C:1]([O:5][CH2:6][CH:7]([OH:23])[CH2:8][C:9]1([OH:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:23][CH:7]([CH2:6][O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:8][C:9]1([OH:22])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 22744586Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 22744588Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.59 g of tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate was dissolved in 10 ml dimethylformamide, 400 mg of sodium hydride and 823 mg of benzyl chloride were added thereto, and the mixture was stirred at room temperature for 20 min. The reaction solution was poured into ice water, extracted with ethyl acetate, washed with water and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was-purified by silica gel column chromatography (hexane/ethyl acetate) to give 2.66 g of tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customthe resulting residue was-purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-423739cdbb4e4befb922f58dbef68633
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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