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

HRID 361783Notes

Reaction equation

HRID 361783 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15](O)=[O:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1.[OH-].[Na+]>C1COCC1>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-BOC-2-(piperidin-4-yl)acetic acid (15.8 g) is dissolved in THF (150 ml) and 1M borane/THF (70 ml) is added dropwise. The solution is stirred at room temperature for about 20 hours and 1N sodium hydroxide solution (200 ml) is added dropwise. The THF is evaporated in vacuo and the aqueousresidue extracted with ethyl acetate. The ethyl acetate solution is washed with water, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-2-(piperidin-4-yl)ethanol.

Workup

  1. customThe THF is evaporated in vacuo
  2. extractionthe aqueousresidue extracted with ethyl acetate
  3. washThe ethyl acetate solution is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8ccccb47e162496ca635df7faaf68819
Source dataset
uspto-grants-1999_02
Patent number
US05866685

Reaction notes

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