Potassium Hydroxide → HCID 58089542, compound

HRID 251484Notes

Reaction equation

HRID 251484 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH2:16][CH2:15][C:14]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH2:19][N:18]([C:26](=[O:28])[CH3:27])[CH2:17]4)[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[K+]>CC(O)=O.O>[C:26]([N:18]1[CH2:17][C:14]2([CH2:13][CH2:12][N:11]([CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)[CH2:16][CH2:15]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11993685HCID 11993685, compound

Product 1

HCID 58089542HCID 58089542, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-(1′-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-spiro[isoquinoline-4,4′-piperidine]-2(3H)-yl)ethanone 6d (350 mg; 0.83 mmol.) was dissolved in 80% aq. AcOH (20 mL) and the solution was refluxed overnight. The reaction mixture was diluted with water (20 mL), cooled on an ice bath and neutralized by addition of solid KOH. The resulting suspension was extracted with DCM (3×30 mL) and the combined organic extracts were dried on Na2SO4 and concentrated to provide the crude 4-(2-acetyl-2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-yl)cyclohexanone 6e (200 mg, 70% yield) as a white foam. LC/MS m/z [M+H]+ 341.0 retention time 1.47 min (10-99% CH3CN—H2O gradient, with 0.05% TFA, 5 min).

Workup

  1. temperaturethe solution was refluxed overnight
  2. temperaturecooled on an ice bath
  3. extractionThe resulting suspension was extracted with DCM (3×30 mL)
  4. customthe combined organic extracts were dried on Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c688aff16b094df5b93ad09dd3584bbb
Source dataset
uspto-grants-2011_01
Patent number
US07863449B2

Reaction notes

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