Potassium Iodide → 1-(Methylcarbonyloxy-methyl)-5-(cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441671Notes

Reaction equation

HRID 1441671 reaction equation
Br[CH2:2][CH:3]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OC[CH2:16][N:17]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:18]1=[O:31])=O.[C:32](=[O:35])([O-])[O-:33].[K+].[K+].[I-].[K+].[C:40](#N)C>>[CH3:40][C:32]([O:33][CH2:16][N:17]1[C:30]2[C:25](=[CH:26][C:27]([CH2:2][CH:3]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[CH:28][CH:29]=2)[C:19]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[C:18]1=[O:31])=[O:35]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 18459730(Bromomethyl)cyclooctaneHCID 588784821-(Methylcarbonyloxy-ethyl)-spiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 685373431-(Methylcarbonyloxy-methyl)-5-(cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

Conditions

Temperature
45 °C

Procedure

1-Bromomethyl-cyclooctane (0.026 g, 0.216 mmol) and 1-(methylcarbonyloxy-ethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.029 g, 0.105 mmol) were dissolved in acetonitrile (1.5 mL). Potassium carbonate (0.044 g, 0.316 mmol) and a catalytic amount of potassium iodide were added and the reaction mixture was stirred at 45° C. under nitrogen atmosphere for 18 hours. The reaction mixture was then partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (3% methanol/dichloromethane) to yield the title compound as an oil.

Workup

  1. customThe reaction mixture was then partitioned with water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude oil
  7. customThe crude oil was purified via flash chromatography (3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-839936d770ef41f1a7c8425a6ccf07e9
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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