Ethanol → trans 2-(3-Amino-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione

HRID 905978Notes

Reaction equation

HRID 905978 reaction equation
[N:1]([C@H:4]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([Cl:20])=[C:14]([Cl:19])[CH:15]=3)[C:10]2=[O:21])[CH2:5]1)=[N+]=[N-].C(O)C>ClCCl>[NH2:1][C@H:4]1[CH2:8][CH2:7][C@H:6]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([Cl:20])=[C:14]([Cl:19])[CH:15]=3)[C:10]2=[O:21])[CH2:5]1

Participants

4

Reactant 2

HCID 702EthanolHCID 86642301Trans 2-(3-azido-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione

Product 1

HCID 86642300trans 2-(3-Amino-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans 2-(3-azido-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione (0.727 g, 2.24 mmol) and lindlar catalyt (0.36 g) was added to a mixture of ethanol and dichloromethane and placed under a hydrogen balloon overnight. The mixture was filtered and the solid rinsed with dichloromethane. The organic layers were concentrated in vacuo, dissolved in methanol and diluted with acetonitrile. The solid was removed by filtration and the filtrate purified by preparative TLC (dichloromethane/methanol/triethylamine). The solid and material from TLC was recrystallized from MeCN/MeOH to give trans 2-(3-amino-cyclopentyl)-5,6-dichloro-isoindole-1,3-dione as an off white solid (0.145 g, contains also trans 2-(3-amino-cyclopentyl)-5-chloro-isoindole-1,3-dione)

Workup

  1. customballoon overnight
  2. filtrationThe mixture was filtered
  3. washthe solid rinsed with dichloromethane
  4. concentrationThe organic layers were concentrated in vacuo
  5. dissolutiondissolved in methanol
  6. additiondiluted with acetonitrile
  7. customThe solid was removed by filtration
  8. customthe filtrate purified by preparative TLC (dichloromethane/methanol/triethylamine)
  9. customThe solid and material from TLC was recrystallized from MeCN/MeOH

Sources & evidence

ORD record
ord-ac725ff4abe24e84b7d149c37934de22
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

Loading…