4-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester → 4-(2-Hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694905Notes

Reaction equation

HRID 1694905 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21]CC2C=CC=CC=2)[CH2:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH2:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 666453984-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 666456104-(2-Hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl esterYield 90.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3.42 g of 4-(2-benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (10c) (8.94 mmol) and 342 mg of 10% palladium-carbon (50% wet) in methanol (90 ml) was stirred under a hydrogen atmosphere at room temperature for six hours. Hydrogen in the reaction vessel was replaced by nitrogen. Then, palladium-carbon was separated by filtration and washed with methanol. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=1/1) to obtain 2.6 g of the title compound (yield: quant.).

Workup

  1. customThen, palladium-carbon was separated by filtration
  2. washwashed with methanol
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6323e01ac34f4de0be07438af4fe2ddf
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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