tert-butyl N-[2-(1-benzyl-4-hydroxypiperidin-4-yl)ethyl]carbamate → tert-butyl N-[2-(4-hydroxypiperidin-4-yl)ethyl]carbamate

HRID 1787699Notes

Reaction equation

HRID 1787699 reaction equation
[OH:1][C:2]1([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4][CH2:3]1>CCO.[OH-].[OH-].[Pd+2]>[OH:1][C:2]1([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 57599590tert-butyl N-[2-(1-benzyl-4-hydroxypiperidin-4-yl)ethyl]carbamate

Product 1

HCID 57599589tert-butyl N-[2-(4-hydroxypiperidin-4-yl)ethyl]carbamateYield 100.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1-dimethylethyl {2-[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]ethyl}carbamate (3.2 g, 9.5 mmol) and Pd(OH)2 (1.92 g, 60 wt %) in EtOH (50 mL) was hydrogenated using a Parr Shaker under 50 psi. After 12 h, the solution was filtered through Celite® and concentrated yielding the title compound (2.33 g, quant.) as a yellow oil: LCMS (ES) m/e 245 (M+H)+.

Workup

  1. filtrationthe solution was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b6d06e660fca422daa7b9cf5d93d7abb
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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