Sodium sulfate decahydrate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1761174Notes

Reaction equation

HRID 1761174 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH:11]([C:12](OCC)=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 516 mg of ethyl N-t-butoxycarbonyl-isonipecotate in 30 ml of tetrahydrofuran, 200 mg of lithium-aluminum hydride was added under cooling with ice, followed by 20 minutes' stirring at the same temperature. Sodium sulfate decahydrate was added to the reaction liquid, stirred for 30 minutes and filtered with Celite. Distilling the solvent off under reduced pressure, 414 mg of the title compound was obtained.

Workup

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

Sources & evidence

ORD record
ord-136ae8d36217411aa8d3769da5052700
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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