Water → HCID 22135707, compound

HRID 344288

Reaction equation

HRID 344288 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([OH:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 22135707HCID 22135707, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate (21 g) in ethanol (20 ml) was added sodium borohydride (9.1 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 9 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 10.55 g of 1-benzyl-3-hydroxy-4-hydroxymethylpiperidine.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1a7410ce394c4b899bbfaa28899ba484
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Linked notes

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