Isatin → HCID 15235503, compound

HRID 2226453Notes

Reaction equation

HRID 2226453 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10](Cl)[CH:9]1C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27].[H-].[Na+].N1C2C(=CC=CC=2)C(=O)[C:31]1=O>O1CCCC1.C(O)(=O)C.O>[OH:27][C:20]1([CH2:31][CH:10]2[CH2:11][CH2:12][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([F:16])[CH:18]=2)[NH:22][C:21]1=[O:26]

Participants

9

Reactant 5

HCID 7054IsatinHCID 24758Sodium hydrideHCID 2365665-FluoroisatinHCID 5462224Magnesium2×HCID 67849385HCID 67849385, compound

Product 1

HCID 15235503HCID 15235503, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of a magnesium compound is prepared, on the one hand, from 334 mmol of 1-benzyl-3-chloro-methylpyrrolidine, 334 mmol of magnesium and 300 ml of tetrahydrofuran (THF). On the other hand, a solution containing [lacuna] is prepared from 303 mmol of 5-fluoroisatin and 303 mmol of sodium hydride in 500 ml of THF. The solution containing the magnesium compound is added at 0° C. to the second solution containing the sodium anion of the isatin. The combined mixture is left for 3 hours at room temperature and then brought to reflux for 12 hours. The reaction mixture is then hydrolyzed while cold with 1 kg of ice and 500 ml of water containing 60 ml of glacial acetic acid. The expected product is then extracted with dichloromethane and obtained in the form of an oil, after drying, evaporation and purification by chromatography on a silica column, using a dichloromethane/methanol/aqueous ammonia (98/2/0.2) mixture as eluent.

Workup

  1. additionOn the other hand, a solution containing [lacuna]
  2. additionis added at 0° C. to the second solution
  3. temperatureto reflux for 12 hours
  4. extractionThe expected product is then extracted with dichloromethane
  5. customobtained in the form of an oil
  6. customafter drying
  7. customevaporation and purification by chromatography on a silica column

Sources & evidence

ORD record
ord-e0ca728f42904873a156d3c17c6e3b28
Source dataset
uspto-grants-1994_09
Patent number
US05348968

Reaction notes

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