Triethylamine → HCID 67463031, compound

HRID 553974Notes

Reaction equation

HRID 553974 reaction equation
[C:1]([N:6]1[C@H:10]([C:11]2[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:12]=2[F:19])[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:16]1[CH:15]=[C:14]([F:18])[CH:13]=[C:12]([F:19])[C:11]=1[C@H:10]1[N:6]2[C@@H:7]([CH:20]=[CH:3][CH2:2][C:1]2=[O:5])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67464673HCID 67464673, compound

Product 1

HCID 67463031HCID 67463031, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl (E)-3-[(2R,5S)-1-(3-butenoyl)-5-(2,4,6-trifluorophenyl)pyrrolidin-2-yl]acrylate (1.35 g) and Grubbs catalyst 2nd generation (155 mg) in methylene chloride (70 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->heptane:ethyl acetate=1:1->ethyl acetate) to obtain 548 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperatureunder reflux for two hours
  2. waitThe reaction solution was left
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (heptane->heptane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record
ord-074647ceba7c462392409a962625f3a6
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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