Potassium Iodide → HCID 23501723, compound

HRID 1835608Notes

Reaction equation

HRID 1835608 reaction equation
CS([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:29][CH:30]=[C:31]([CH2:33][CH2:34]O)[CH:32]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CS(C)=O.C(C(C)=O)C>[CH2:33]([C:31]1[CH:32]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[C:28]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:29][C:30]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)[CH3:34]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylateHCID 23501712HCID 23501712, compound

Product 1

HCID 23501723HCID 23501723, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(Methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine (143 mg, 0.49 mmol) and 5-(4-fluorophenyl)-4-benzyloxy-2-hydroxyethylbenzene (150 mg, 0.47 mmol) were added to methyl ethyl ketone (7 mL) followed by potassium carbonate (113 mg, 0.82 mmol), potassium iodide (15.5 mg, 93 μmol), and dimethylsulfoxide (4 mL). The slurry was heated at reflux for 40 hours, when it was cooled, diluted with water (50 mL) and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to a clear oil which was not purified but used as is in the following step. Mass Spec (EI): 537.4 (M+NH4)

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 40 hours
  3. temperaturewhen it was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to a clear oil which
  8. customwas not purified

Sources & evidence

ORD record
ord-c77de8585c4b4509b1b5088273cfd120
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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