Sodium sulfate decahydrate → tert-Butyl (3R)-3-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 1761179Notes

Reaction equation

HRID 1761179 reaction equation
C([O:3][C:4](=O)[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[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][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 29919087(R)-1-Boc-3-piperidine acetate ethyl ester

Product 1

HCID 40425180tert-Butyl (3R)-3-(2-hydroxyethyl)piperidine-1-carboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 143 mg of t-butyl(3R)-3-(2-ethoxy-2-oxoethyl)tetrahydropyridine-1(2H)-carboxylate in 5 ml of tetrahydrofuran, 30 mg of litiumaluminum 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 12 hours and filtered with Celite. Distilling the solvent off under reduced pressure, 118 mg of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. stirringstirred for 12 hours
  4. filtrationfiltered with Celite
  5. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-1dd0d357d23e4e5585affb32963645e5
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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