1-Benzyl 4-ethyl (2S)-2-methylpiperazine-1,4-dicarboxylate → Ethyl (3S)-3-methylpiperazine-1-carboxylate

HRID 1970548

Reaction equation

HRID 1970548 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[C@@H:8]([CH3:22])[CH2:7]1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([CH3:22])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668543581-Benzyl 4-ethyl (2S)-2-methylpiperazine-1,4-dicarboxylate

Product 1

HCID 11298228Ethyl (3S)-3-methylpiperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3.5 g (S)-2-Methyl-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester and 0.4 g Pd/C (10%) in 56 ml ethyl acetate was stirred under an atmosphere of hydrogen (3 bar) for 12 h. The mixture was filtrated over a plug of Celite, washed with ethyl acetate and the combined wash solutions concentrated to give the title compound as colourless oil. Yield: 1.6 g.

Workup

  1. filtrationThe mixture was filtrated over a plug of Celite
  2. washwashed with ethyl acetate
  3. concentrationthe combined wash solutions concentrated

Sources & evidence

ORD record
ord-c8abda605ef24fc0b6aa8ee91a682fee
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Linked notes

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