Water → HCID 22678362, compound

HRID 1837715Notes

Reaction equation

HRID 1837715 reaction equation
[Cl-].[CH:2]1([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH2:38]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51]([CH:54]=O)[CH2:50][CH2:49]1)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.O>CS(C)=O.O1CCCC1>[CH2:38]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51](/[CH:54]=[CH:16]/[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[CH2:50][CH2:49]1)=[O:47])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2776272Benzyl 4-formylpiperidine-1-carboxylateHCID 22678452HCID 22678452, compound

Product 1

HCID 22678362HCID 22678362, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1.75 g of [[2-(cyclohexylmethyloxy)phenyl]methyl]triphenylphosphonium chloride was dissolved in 10 ml of dimethyl sulfoxide, 144 mg of 60% sodium hydride was added thereto, and the mixture was stirred at 70° C. After leaving to cool to room temperature, a solution of 800 mg of 1-(benzyloxycarbonyl)-4-piperidinecarboxaldehyde dissolved in 3 ml of tetrahydrofuran was added dropwise thereinto and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N-hydrochloric acid, an aqueous saturated sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 554 mg of the title compound as a colorless oil.

Workup

  1. customAfter leaving
  2. temperatureto cool to room temperature
  3. additionwas added dropwise
  4. stirringthe mixture was stirred at room temperature for one hour
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with 1N-hydrochloric acid
  7. dry with materialan aqueous saturated sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d4fbe75806c2474ba7642dee2c7d8f6f
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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