1-Benzyl-3-methyl-4-piperidone → 1-Benzyl-3-methylpiperidin-4-ol

HRID 1867396Notes

Reaction equation

HRID 1867396 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 4311764Sodium borohydride

Product 1

HCID 136114921-Benzyl-3-methylpiperidin-4-olYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl-3- methyl-piperidin-4-one (2.0 g, 10 mmol) was dissolved in MeOH (10 ml), cooled to 0° C. and sodium borohydride (0.2 g, 5 mmol) was added portionwise. The reaction was allowed to reach room temperature and stirred overnight after which time the solvent was removed under vacuum, the residue redissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated to afford the title compound (2.1 g, quant), a 3:1 mixture of diasteriomers (trans:cis) as gum. MS: 206.2 (MH+).

Workup

  1. customto reach room temperature
  2. customwas removed under vacuum
  3. dissolutionthe residue redissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11463f45e6604c3e94b264e4044cc1bd
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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