Hydrochloric Acid → cis 5,6-dichloro-2-(3-hydroxy-cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-diol

HRID 905976Notes

Reaction equation

HRID 905976 reaction equation
Cl.C([Si](C)(C)[O:7][C@@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17]([Cl:24])=[C:18]([Cl:23])[CH:19]=3)[C:14]2=[O:25])[CH2:9]1)(C)(C)C>CO>[Cl:24][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][C:18]=1[Cl:23])[C@H:21]([OH:22])[N:13]([CH:10]1[CH2:11][CH2:12][CH:8]([OH:7])[CH2:9]1)[C@@H:14]2[OH:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86642299cis 2-[3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-5,6-dichloro-isoindole-1,3-dione

Product 1

HCID 86642298cis 5,6-dichloro-2-(3-hydroxy-cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-diolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing HCl (37%, 5 mL) and methanol (155 mL) was added cis 2-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-5,6-dichloro-isoindole-1,3-dione (1.7 g, 4.1 mmol). The mixture was placed in an ultrasound bath until all of the solid had dissolved (15 minutes) then evaporated to give cis 5,6-dichloro-2-(3-hydroxy-cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-diol (1.172 g, 95% yield).

Workup

  1. customThe mixture was placed in an ultrasound bath
  2. dissolutionuntil all of the solid had dissolved (15 minutes)
  3. customthen evaporated

Sources & evidence

ORD record
ord-521a801c7ed34afcada032c451ed7c5b
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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