HCID 22341850, compound → HCID 22182264, compound

HRID 584857Notes

Reaction equation

HRID 584857 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:7][C:6](=[O:8])[CH2:5][C:4]([CH2:11][CH3:12])([CH2:9][CH3:10])[NH:3]1>CO>[CH3:13][C:2]1([CH3:1])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH2:9][CH3:10])([CH2:11][CH3:12])[NH:3]1

Participants

3

Reactant 1

HCID 22341850HCID 22341850, compound

Product 1

HCID 22182264HCID 22182264, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 15.8 g (0.086 mol) 2,2-dimethyl-6,6-diethyl-4-oxopiperidine in 50 ml methanol 2.2 g (0.06 M) sodium borohydride are added in portions. The temperature is kept below 30° C. After stirring over night methanol is removed under vacuum and the residue is diluted with 20 ml 2N-NaOH. The solution is extracted with ethylacetate. The combined extracts are washed with saturated NaCl solution, dried over MgSO4 and dried under vacuum at 60° C./50 mbar until a constant weight is achieved. 15.8 g (99%) 2,2-dimethyl-6,6-diethyl-4-hydroxypiperidine are obtained as yellowish oil.

Workup

  1. customis kept below 30° C
  2. customis removed under vacuum
  3. additionthe residue is diluted with 20 ml 2N-NaOH
  4. extractionThe solution is extracted with ethylacetate
  5. washThe combined extracts are washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customdried under vacuum at 60° C./50 mbar until a constant weight

Sources & evidence

ORD record
ord-5ccbba85043447e5a9e65d5d28abde8e
Source dataset
uspto-grants-2005_08
Patent number
US06927295B2

Reaction notes

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