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

HRID 1007746Notes

Reaction equation

HRID 1007746 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 1 M 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 aqueous residue extractred 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. washThe ethyl acetate solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c756f040a5d44ed784c37abad5f35084
Source dataset
uspto-grants-2004_09
Patent number
US06797700B2

Reaction notes

Loading…