Sodium borohydride → 1-Benzyl-3,3-dimethylpiperidin-4-OL

HRID 1867397Notes

Reaction equation

HRID 1867397 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([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])[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 224957201-Benzyl-3,3-dimethylpiperidin-4-OLYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl-3,3-dimethyl-piperidin-4-one (WO 01/00577 A2) (5.0 g, 23 mmol) was dissolved in MeOH (25 ml), cooled to 0° C. and sodium borohydride (1.0 g, 25 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 (4.9 g, 97%). MS: 220.4 (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-5b8e9b4bca5b44238c29af762b0cf80a
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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