Formic Acid → tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate

HRID 1038559Notes

Reaction equation

HRID 1038559 reaction equation
C([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:10]([CH3:22])[CH2:9]1)C1C=CC=CC=1.C(O)=O>CO.[C].[Pd]>[CH3:22][C@@H:10]1[CH2:9][NH:8][C@@H:13]([CH3:14])[CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 54474705HCID 54474705, compound

Product 1

HCID 24903576tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylateYield 110.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Under an argon atmosphere, (2R,5S)-tert-butyl 4-benzyl-2,5-dimethylpiperazine-1-carboxylate (2.0 g, 6.57 mmol) was dissolved in methanol (60 mL), and added 10% palladium carbon (670 mg) and formic acid (1.5 g, 32.9 mmol). The mixture was stirred at room temperature for 2 hours. Then, the reaction solution was filtered through a pad of celite, and concentrated in vacuo. The obtained residue was added chloroform and a saturated aqueous solution of sodium hydrogen carbonate, extracted with chloroform, dried over sodium sulfate, concentrated in vacuo, and the title compound (1.56 g, >100%) was obtained as a yellow oil.

Workup

  1. filtrationThen, the reaction solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. additionThe obtained residue was added chloroform
  4. extractiona saturated aqueous solution of sodium hydrogen carbonate, extracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f4851f46b21413191965a6672c7fd25
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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