4-(1-Ethoxycarbonylcyclopropyl)-3-fluoro-1-[1-(S)-phenylethyl1-3-pyrrolin-2-one → 4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone

HRID 635110ノート

反応式

HRID 635110 の反応式
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[O:22])[C:10]=2[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[C:11](=[O:22])[C@H:10]2[F:23])[CH2:7][CH2:8]1)=[O:5])[CH3:2]

参加物

4

反応物 1

HCID 99229604-(1-Ethoxycarbonylcyclopropyl)-3-fluoro-1-[1-(S)-phenylethyl1-3-pyrrolin-2-one

生成物 1

HCID 109692184-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone収率 64.7%

試薬・触媒・溶媒 2

HCID 935Nickel触媒2 回HCID 702Ethanol溶媒

実験手順

To a solution of 4-(1-ethoxycarbonylcyclopropyl)-3-fluoro-1-[1-(S)-phenylethyl]-3-pyrrolin-2-one (587 mg, 1.85 mmol) in ethanol (5 ml) was added Raney nickel (R-100, 2 ml). Under a hydrogen atmosphere of 5 kg/cm2, the mixture was stirred at room temperature for 1 hour. Next, Raney nickel (R-100, 3 ml) was further added and stirring was continued under the same conditions for 2.5 hours. After eliminating the catalyst by filtering through celite (washed with ethanol), the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel column chromatography (eluent: n-hexane:ethyl acetate=3:1) to obtain 382 mg (64.6%) of the title compound as a colorless oily substance. The 1H-NMR data of this compound agreed with the data of the compound obtained in Referential Example 10-2.

後処理

  1. stirringstirring
  2. waitwas continued under the same conditions for 2.5 hours
  3. filtrationby filtering through celite (washed with ethanol)
  4. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-00cc6a3f76374c128e206a01ae428fc2
出典データセット
uspto-grants-2001_02
特許番号
US06184388B2

反応ノート

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