Water → HCID 69481139, compound

HRID 856260Notes

Reaction equation

HRID 856260 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)C=CC=CC=1.[H-].[Na+].[CH:34]([O:36][CH:37]1[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])[CH2:39][CH2:38]1)=O.O>CS(C)=O>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:12]=[CH:11][C:10]([CH:9]=[CH:34][O:36][CH:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])[CH2:39][CH2:38]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10391293Phosphonium, triphenyl[[4-(trifluoromethyl)phenyl]methyl]-, bromideHCID 23081105HCID 23081105, compound

Product 1

HCID 69481139HCID 69481139, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Triphenyl-(4-trifluoromethylbenzyl)-phosphonium bromide (3.00 g, 5.98 mmol) was dissolved in DMSO (50 ml). To the solution, sodium hydride (0.239 g, 5.98 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 1 hour. To the solution, a solution of benzyl 4-formyloxypiperidine-1-carboxylate (1.497 g, 5.69 mmol) in DMSO (10 ml) was added dropwise followed by stirring at 60° C. for 7 hours. The reaction mixture was added water and extracted with ethyl acetate twice. The organic phases were combined, washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) and then purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford benzyl 4-[2-(4-trifluoromethylphenyl)-vinyloxy]piperidin-1-carboxylate as a colorless oil.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringby stirring at 60° C. for 7 hours
  3. extractionextracted with ethyl acetate twice
  4. washwashed with water
  5. dry with materiala saturated saline solution, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)
  9. custompurified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-3ac4869a05644bb4a68cb91756716cd0
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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