Dichloromethane → (4R,9aS)-4-(3,4,5-trifluorophenyl)-3,4,7,9a-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-6-one

HRID 16349Notes

Reaction equation

HRID 16349 reaction equation
ClCCl.COC(=O)/[CH:7]=[CH:8]/[C@H:9]1[CH2:14][O:13][CH2:12][C@@H:11]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)[N:10]1[C:24](=[O:28])[CH2:25]C=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:11]2[CH2:12][O:13][CH2:14][C@@H:9]3[CH:8]=[CH:7][CH2:25][C:24](=[O:28])[N:10]23)[CH:16]=[C:17]([F:23])[C:18]=1[F:22]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67463888methyl (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate

Product 1

HCID 67464206(4R,9aS)-4-(3,4,5-trifluorophenyl)-3,4,7,9a-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-6-oneYield 26.3%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Grubbs catalyst second generation (285 mg) was added to a dichloromethane solution (100 mL) of (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylic acid methyl ester (1.24 g). The resulting reaction solution was heated under reflux for 1.5 hr in nitrogen atmosphere. The reaction solution was cooled to room temperature, and triethylamine (3 mL) was added thereto. The resulting reaction solution was stirred for 10 min and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 250 mg of the title compound. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux for 1.5 hr in nitrogen atmosphere
  4. customThe resulting reaction solution
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-c6302112cfe44d9faded016d5dbbbe7b
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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