HCID 717394, compound → HCID 22106486, compound

HRID 1941489Notes

Reaction equation

HRID 1941489 reaction equation
CC(C)([O-:4])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]([C@@H:14]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][C@H:15]2[N+]([O-])=O)[CH:11]=[CH:12][CH:13]=1>ClCCl.CO>[Br:7][C:8]1[CH:9]=[C:10]([CH:14]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][C:15]2=[O:4])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 717394HCID 717394, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22106486HCID 22106486, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium t-butoxide (38.7 g) was added to a stirred solution of the trans-6-(3-bromo-phenyl)-5-nitro-piperidin-2-one (96.3 g) in dichloromethane (500 ml) and methanol (500 ml). The mixture was cooled to -70° and ozone was vigorously bubbled through the stirred solution for 7 h. The mixture was purged with nitrogen and pH6.5 phosphate buffer (500 ml) added. Sodium thiosulphate (120 g) and water (500 ml) were added and the mixture stirred as it warmed to room temperature overnight. The mixture was tested for peroxides then extracted with dichloromethane (600 ml×3). The combined organic extracts were washed with water (500 ml) then saturated brine (500 ml), dried (MgSO4) and evaporated in vacuo. Trituration with ether and hexane gave the title compound as a white solid (70.0 g). T.l.c. (Ethyl acetate) Rf 0.43.

Workup

  1. temperatureThe mixture was cooled to -70°
  2. customozone was vigorously bubbled through the stirred solution for 7 h
  3. customThe mixture was purged with nitrogen and pH6.5 phosphate buffer (500 ml)
  4. additionadded
  5. additionSodium thiosulphate (120 g) and water (500 ml) were added
  6. extractionthen extracted with dichloromethane (600 ml×3)
  7. washThe combined organic extracts were washed with water (500 ml)
  8. dry with materialsaturated brine (500 ml), dried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-2053750e7d6a4753bf569139f506fa46
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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