Formic Acid → (2S,5R)-1-Boc-2,5-dimethylpiperazine

HRID 1038560Notes

Reaction equation

HRID 1038560 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 66598992(2S,5R)-4-Benzyl-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11745988(2S,5R)-1-Boc-2,5-dimethylpiperazineYield 101.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(2S,5R)-tert-butyl 4-benzyl-2,5-dimethylpiperazine-1-carboxylate (3.11 g, 10.2 mmol) was dissolved in methanol (19 mL), added palladium carbon (156 mg) under an argon atmosphere, and added formic acid (2.4 g, 51.1 mmol) under ice-cold conditions. The solution was reverted to room temperature, and stirred overnight. Then, the reaction solution was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The obtained residue was added water and hexane, and extracted. An aqueous solution of sodium hydroxide was added to the aqueous layer, extracted with 2-methyltetrahydrofuran, dried over anhydrous sodium sulfate, concentrated in vacuo, and the title compound (2.21 g (yield >100%)) was obtained as a colorless oil.

Workup

  1. customwas reverted to room temperature
  2. filtrationThen, the reaction solution was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe obtained residue was added water and hexane
  5. extractionextracted
  6. additionAn aqueous solution of sodium hydroxide was added to the aqueous layer
  7. extractionextracted with 2-methyltetrahydrofuran
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ef19673402e4c90b27aeb4de2f175a9
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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