Hydrochloric Acid → ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate

HRID 1436090Notes

Reaction equation

HRID 1436090 reaction equation
[Cl-].[C:2]([O:7][CH2:8][CH3:9])(=[O:6])[C:3]([O-:5])=O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([CH:23]=[CH2:24])[NH:18]2)=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.C(Cl)(Cl)Cl>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([CH:23]=[CH2:24])[N:18]2[C:3](=[O:5])[C:2]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 22632797HCID 22632797, compoundHCID 69010346(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine

Product 1

HCID 86612603ethyl [(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]oxoacetate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl oxalate chloride (0.5 mL) was added to a solution of (2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine (520 mg) and DIEA (0.66 mL) in methylene chloride (10 mL), and the reaction solution was stirred at room temperature for one hour. Chloroform 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 426 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-e0891c4a2f904957a2c1f394155ee862
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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