HCID 13908798, compound → (2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-one

HRID 1987801Notes

Reaction equation

HRID 1987801 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]([CH3:19])=[CH2:18])[CH2:15][C:14](=O)[CH2:13][CH:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[OH-:28].[NH4+:29].Cl>CCO.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C@H:16]([C:17]([CH3:19])=[CH2:18])[CH2:15]/[C:14](=[N:29]/[OH:28])/[CH2:13][C@H:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13908798HCID 13908798, compoundHCID 68904372rac-(1S,2S,6R)-6'-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3'-[3H]indole]-2',4(1'H)-dione

Product 1

HCID 140531877(2'S,3S,4'Z,6'S)-6-bromo-2'-(3-chlorophenyl)-4'-hydroxyimino-6'-prop-1-en-2-ylspiro[1H-indole-3,1'-cyclohexane]-2-oneYield 75.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The suspension of rac-(1S,2S,6R)-6′-bromo-2-(3-chlorophenyl)-6-isopropenyl spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (0.23 g, 0.52 mmol) and NH4OH—HCl (0.1 g, 0.52 mmol) in EtOH-water (3/2, 20 mL) was allowed to reflux for 1 h. TLC analysis indicated the formation of desired product and complete consumption of starting material. The reaction was cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:2, then 1:1) to give the title compound as a white solid (0.18 g, 75%): HRMS (ES+) m/z Calcd for C22H20BrClN2O2+H [(M+H)+]: 459.0470, Found: 459.0470.

Workup

  1. temperatureto reflux for 1 h
  2. customthe formation of desired product and complete consumption of starting material
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-e626ec31474d466fb7e6a5543b68a760
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

Loading…