Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

HRID 553893Notes

Reaction equation

HRID 553893 reaction equation
C(P(=O)(OCC)OCC)#N.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C@H:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([CH:27]=[CH2:28])[NH:22]2)=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12].[CH:29]([CH2:31][C:32](O)=[O:33])=[CH2:30].Cl>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C@H:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([CH:27]=[CH2:28])[N:22]2[C:32](=[O:33])[CH2:31][CH:29]=[CH2:30])=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69072776(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidine

Product 1

HCID 690737051-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl cyanophosphonate (0.78 mL) was added to a solution of (2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidine (422 mg), vinylacetic acid (0.44 mL), and triethylamine (1.44 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 281 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-40f83c110b2345d3bf11d6d42540e239
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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