Water → HCID 118598738, compound

HRID 1050427Notes

Reaction equation

HRID 1050427 reaction equation
[Br:1][C:2]1[C:3](=[O:23])[N:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[C:7](=[O:12])[CH:6](C(OCC)=O)[C:5]12[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[Li+].O>CS(C)=O>[Br:1][C:2]1[C:3](=[O:23])[N:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[C:7](=[O:12])[CH2:6][C:5]12[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 118598902HCID 118598902, compound

Product 1

HCID 118598738HCID 118598738, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 6′-bromo-8′-methyl-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-indolizine]-2′-carboxylate (6, 1.0 mmol, 1.0 eq) in dimethylsulfoxide (15 mL) add lithium chloride (5.0 mmol, 5 eq) and heat the reaction at 140° C. for 16 h. After completion cool the reaction, add water and extract with dichloromethane. Remove the solvent under reduced pressure and purify the crude by silica gel column chromatography to get 6′-bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-indolizine]-1′,5′-dione (7).

Workup

  1. temperatureheat
  2. customthe reaction at 140° C. for 16 h
  3. temperatureAfter completion cool
  4. customthe reaction
  5. extractionextract with dichloromethane
  6. customRemove the solvent under reduced pressure
  7. custompurify the crude by silica gel column chromatography

Sources & evidence

ORD record
ord-bae5fbc8bf234e05a3d2b840cfda2f05
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…