2-Benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline → 4-(t-Butyloxycarbonylaminomethyl)isoindoline

HRID 1494852Notes

Reaction equation

HRID 1494852 reaction equation
C(OC([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:25]([O:24][C:22]([NH:21][CH2:20][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[CH2:19][NH:11][CH2:12]2)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 198284932-Benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline

Product 1

HCID 198284894-(t-Butyloxycarbonylaminomethyl)isoindolineYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.44 g of 2-benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline was dissolved in 50 ml of methanol. 200 mg of 10% palladium on carbon was added to it and the mixture was stirred under hydrogen gas stream for 3 days. After removing the catalyst by filtration, the filtrate was concentrated and the residue was recrystallized from ether to give 1.75 g of 4-(tertbutyloxycarbonylaminomethyl)isoindoline.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated
  4. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-2693d69de44945c9b6d011c72cfc48f8
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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