1,1-Dimethylethyl 2-(2-hydroxyethyl)-4-(phenylmethyl)-1-piperazinecarboxylate → tert-Butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 750466Notes

Reaction equation

HRID 750466 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]([CH2:21][CH2:22][OH:23])[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH2:21][CH2:22][OH:23])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 189329551,1-Dimethylethyl 2-(2-hydroxyethyl)-4-(phenylmethyl)-1-piperazinecarboxylate

Product 1

HCID 18933038tert-Butyl 2-(2-hydroxyethyl)piperazine-1-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (RS)-4-benzyl-1-(tert-butyloxycarbonyl)-2-(2-hydroxyethyl)piperazine (D5) (2.5 g, 7.81 mmol) in ethanol (150 ml) was hydrogenated at atmospheric pressure and room temperature in the presence of 10% palladium on charcoal (2.07 g, 54% paste with water) for 3.5 h. The mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to give the title compound as a colourless oil (1.65 g, 92%). Mass spectrum (AP+): Found 231 (MH+). C11H22N2O3 requires 230.

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-388c55d8388a4e869f907bfa1673b9ae
Source dataset
uspto-grants-2008_07
Patent number
US07405217B2

Reaction notes

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