(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid Benzyl Ester → Perindopril

HRID 273482Notes

Reaction equation

HRID 273482 reaction equation
[CH3:1][CH2:2][CH2:3][C@H:4]([NH:10][C@H:11]([C:13]([N:15]1[C@@H:23]([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH2:22][C@H:21]2[C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H]>C(O)C.[Pd]>[CH3:1][CH2:2][CH2:3][C@H:4]([NH:10][C@H:11]([C:13]([N:15]1[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][C@H:21]2[C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 71751530(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic Acid Benzyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 107807Perindopril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The Perindopril benzyl ester (2.9 g, 6.33 mmoles) dissolved in ethyl alcohol (15 ml) hydrogenated using 10% Palladium on carbon (0.29 g), under 45-50 psi hydrogen pressure for 2.5-3 hrs. The reaction was performed at 25-30° C. After completion of the reaction, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure to afford Perindopril as a viscous oil.

Workup

  1. customwas performed at 25-30° C
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b27007e3df74896829f71300b2106d2
Source dataset
uspto-grants-2008_11
Patent number
US07456296B2

Reaction notes

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