Triethylamine → methyl (4R*,9aS*)-6-oxo-4-(3,4,5-trifluorophenyl)-1,3,4,6,7,9a-hexahydropyrido[1,2-a]pyrazine-2-carboxylate

HRID 554008Notes

Reaction equation

HRID 554008 reaction equation
[C:1]([N:6]1[CH:11]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=2)[CH2:10][N:9]([C:21]([O:23][CH3:24])=[O:22])[CH2:8][CH:7]1[CH:25]=CC(OCC)=O)(=[O:5])[CH2:2][CH:3]=C.C(N(CC)CC)C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[O:5]=[C:1]1[N:6]2[C@H:11]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=3)[CH2:10][N:9]([C:21]([O:23][CH3:24])=[O:22])[CH2:8][C@@H:7]2[CH:25]=[CH:3][CH2:2]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67465156Methyl 4-(3-butenoyl)-3-(2-ethoxycarbonylvinyl)-5-(3,4,5-trifluorophenyl)piperazine-1-carboxylate

Product 1

HCID 67463345methyl (4R*,9aS*)-6-oxo-4-(3,4,5-trifluorophenyl)-1,3,4,6,7,9a-hexahydropyrido[1,2-a]pyrazine-2-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Grubbs catalyst 2nd generation (124 mg) was added to a solution of methyl 4-(3-butenoyl)-3-(2-ethoxycarbonylvinyl)-5-(3,4,5-trifluorophenyl)piperazine-1-carboxylate (643 mg) in methylene chloride (50 mL), and the reaction solution was heated under reflux for one hour. The reaction solution was left to cool to room temperature. Then, triethylamine (0.2 mL) was added to the reaction solution, which was then stirred at room temperature for 20 minutes. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain 174 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for one hour
  3. waitThe reaction solution was left
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a9781196dcf84e90823cd4c057115cc5
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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