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 635110노트

반응식

HRID 635110 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매2회HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00cc6a3f76374c128e206a01ae428fc2
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184388B2

반응 노트

불러오는 중…