Dichloromethane → (3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-one

HRID 16337Notes

Reaction equation

HRID 16337 reaction equation
C(Cl)Cl.C(OC(=O)/C=C/[C@H:10]1[CH2:14][CH2:13][C@@H:12]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[N:11]1[C:24](=[O:28])[CH2:25][CH:26]=[CH2:27])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(N(CC)CC)C>[F:21][C:19]1[CH:20]=[C:15]([C@H:12]2[N:11]3[C@@H:10]([CH:27]=[CH:26][CH2:25][C:24]3=[O:28])[CH2:14][CH2:13]2)[CH:16]=[C:17]([F:23])[C:18]=1[F:22]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67461604ethyl (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]acrylate

Product 1

HCID 67466164(3S,8aR)-3-(3,4,5-trifluorophenyl)-2,3,6,8a-tetrahydro-1H-indolizin-5-oneYield 70.3%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A methylene chloride solution (60 mL) of (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]acrylic acid ethyl ester (1.33 g) and Grubbs catalyst second generation (153 mg) was heated under reflux for 2 hr. The reaction solution was allowed to cool to room temperature, and then triethylamine (0.5 mL) was added thereto. The resulting mixture was stirred for 1 hr and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1) to give 680 mg of the title compound. The physical property values of this compound were as follows:

Workup

  1. temperatureunder reflux for 2 hr
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1)

Sources & evidence

ORD record
ord-45406d9f1d164b6cac2410eba786d7af
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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