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

HRID 16349ノート

反応式

HRID 16349 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178425456HCID 178425456、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-c6302112cfe44d9faded016d5dbbbe7b
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

反応ノート

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