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

HRID 16349노트

반응식

HRID 16349 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178425456HCID 178425456, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-c6302112cfe44d9faded016d5dbbbe7b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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