Triethylamine → (3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one
Reaction equation
[C:1]([N:6]1[C@H:10]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[C:13]([F:19])[CH:12]=2)[CH2:9][CH2:8][C@@H:7]1/[CH:20]=C/C(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>[F:17][C:15]1[CH:16]=[C:11]([C@H:10]2[N:6]3[C@@H:7]([CH:20]=[CH:3][CH2:2][C:1]3=[O:5])[CH2:8][CH2:9]2)[CH:12]=[C:13]([F:19])[C:14]=1[F:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ethyl (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]acrylate (1.33 g) and Grubbs catalyst 2nd generation (153 mg) in methylene chloride (60 mL) was heated under reflux for two hours. The reaction solution was left to cool to room temperature. Then, triethylamine (0.5 mL) was added to the reaction solution, and the mixture was stirred for one hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1->ethyl acetate) to obtain 680 mg of the title compound. The property values of the compound are as follows.
Workup
- temperatureunder reflux for two hours
- waitThe reaction solution was left
- concentrationThe reaction solution was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1->ethyl acetate)
Sources & evidence
- ORD record
- ord-fabd70dba18842e0973f3001c21d5a18
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048878B2
Reaction notes
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