HCID 69677712, compound → HCID 54493713, compound

HRID 584203Notes

Reaction equation

HRID 584203 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])[C@H:10]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([CH3:29])[CH:23]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-].[C]>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([CH3:29])[CH:23]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 69677712HCID 69677712, compound

Product 1

HCID 54493713HCID 54493713, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of (2R)-4-benzyl-1-tert-butoxycarbonyl-2-(3,4-dimethylbenzyl)piperazine (48.5 g) in methanol (730 ml) was hydrogenated over 20% palladium hydroxide-carbon (0.3 g) at room temperture under atmospheric pressure. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (10:1). The fractions containing the objective compound was collected and evaporated under reduced pressure to give an oil of (2R)-1-tert -butoxycarbonyl-2-(3,4-dimethylbenzyl)piperazine (33.7 g).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (10:1)
  5. additionThe fractions containing the objective compound
  6. customwas collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9bc1166ac99448aeb10991882223faab
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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