HCID 22341850, compound → HCID 22182264, compound

HRID 276121Notes

Reaction equation

HRID 276121 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-95b825b6228445f5a3e9eecdb27d2695
Source dataset
uspto-grants-2002_03
Patent number
US06353107B1

Reaction notes

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