Sodium sulfate decahydrate → 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

HRID 458754Notes

Reaction equation

HRID 458754 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 9993342Ethyl 1-((1,1-dimethylethoxy)carbonyl)-4-piperidineacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 263 mg of t-butyl 4-(2-ethoxy-2-oxoethyl)-tetrahydropyridine-1(2H)-carboxylate in 15 ml of tetrahydrofuran, 100 mg of lithiumaluminum hydride was added under cooling with ice, followed by 20 minutes' stirring at the same temperature. To the reaction liquid sodium sulfate decahydrate was added, stirred for 30 minutes and filtered with Celite. Distilling the solvent off under reduced pressure, 207 mg of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. stirringstirred for 30 minutes
  4. filtrationfiltered with Celite
  5. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-95321922b76748fd9e7d076eceb7b817
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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