Triethylamine → HCID 67464899, compound

HRID 553998Notes

Reaction equation

HRID 553998 reaction equation
[C:1]([N:6]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:10][O:9][CH2:8][C@@H:7]1/[CH:19]=[CH:20]/[C:21](OC)=O)(=[O:5])CC=C.C(N1[C@H](C2C=CC(Cl)=CC=2)COC[C@@H]1/C=C\C(OC)=O)(=O)CC=C.C(N(CC)CC)C.[H][H]>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl.CO.[Pt]=O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C@@H:11]2[CH2:10][O:9][CH2:8][C@@H:7]3[CH2:19][CH2:20][CH2:21][C:1](=[O:5])[N:6]23)=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 67459992HCID 67459992, compoundHCID 67460813HCID 67460813, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67464899HCID 67464899, compound

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 178425456HCID 178425456, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Grubbs catalyst 2nd generation (21.3 mg) was added to a solution of methyl 3-[(3S,5R)-4-but-3-enoyl-5-(4-chlorophenyl)morpholin-3-yl]-(E)-acrylate and methyl 3-[(3S,5R)-4-but-3-enoyl-5-(4-chlorophenyl)morpholin-3-yl]-(Z)-acrylate (87.9 mg) in dichloromethane (10 mL), and the reaction solution was heated under reflux in a nitrogen atmosphere for 1.5 hours. The reaction solution was returned to room temperature. Triethylamine (500 μL) was added to the reaction solution, which was then stirred for 10 minutes. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain a crude product. Platinum oxide (6.02 mg) was added to a solution of the crude product in methanol (3 mL), and the reaction solution was stirred in a hydrogen atmosphere at room temperature for one hour. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system) to obtain 48.7 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for 1.5 hours
  3. customwas returned to room temperature
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)
  6. customto obtain a crude product
  7. filtrationThe reaction solution was filtered through celite
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-4cb5230ac4294d6aac79e0262c239b5a
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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