(S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester → tert-Butyl (2S)-2-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 1963069Notes

Reaction equation

HRID 1963069 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10][C@@H:9]1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67772911(S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Product 1

HCID 29414379tert-Butyl (2S)-2-(2-methoxy-2-oxoethyl)piperazine-1-carboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To the compound of step 2 (2.317 g, 5.90 mmol) in 40 ml of MOH was added 0.063 g of 10% palladium on charcoal and the mixture was hydrogenated under a hydrogen pressure of 4 bar for 45 min at room temperature. The catalyst was filtered off and the filtrate evaporated to dryness under reduced pressure. 1.488 g of the title compound were obtained as a pale grey oil.

Workup

  1. customfor 45 min
  2. customat room temperature
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4fa4312ed19849bd964f9bb2311df1bb
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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