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

HRID 553964ノート

反応式

HRID 553964 の反応式
[C:1]([N:6]1[C@H:11]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=2)[CH2:10][O:9][CH2:8][C@@H:7]1/[CH:21]=[CH:22]/[C:23](OC)=O)(=[O:5])CC=C.C(N1[C@H](C2C=C(F)C(F)=C(F)C=2)COC[C@@H]1/C=C\C(OC)=O)(=O)CC=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.ClCCl>[F:18][C:16]1[CH:17]=[C:12]([C@@H:11]2[CH2:10][O:9][CH2:8][C@@H:7]3[CH:21]=[CH:22][CH2:23][C:1](=[O:5])[N:6]23)[CH:13]=[C:14]([F:20])[C:15]=1[F:19]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 67461698methyl (Z)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylateHCID 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 114.7%

試薬・触媒・溶媒 2

HCID 178425456HCID 178425456、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

Grubbs catalyst 2nd generation (27.7 mg) was added to a solution of methyl (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate (109.8 mg) and methyl (Z)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylate (132.5 mg) in dichloromethane (12 mL), and the reaction solution was heated under reflux in a nitrogen atmosphere for one hour. The reaction solution was returned to room temperature. Triethylamine (0.5 mL) was added to the reaction solution, which was then stirred for 10 minutes. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate) to obtain 96.6 mg of the title compound.

後処理

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux in a nitrogen atmosphere for one hour
  3. customwas returned to room temperature
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate)

出典と根拠

ORDレコード
ord-e924d50280184e98b1de8cb9c25905ad
出典データセット
uspto-grants-2011_11
特許番号
US08048878B2

反応ノート

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