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Triphenyl phosphite → (S)-methyl6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate

HRID 69579
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HRID 69579 반응식
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[C:19]([N+:20]([O-])=O)=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[O:2]=[C:3]1[NH:20][C:19]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[N:11][C:10]=2[N:6]2[CH2:7][CH2:8][CH2:9][C@@H:5]12
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참가 물질

6

반응물 2

HCID 7540Triphenyl phosphiteHCID 58324504(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate

생성물 1

HCID 58324449(S)-methyl6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate수율 80%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매
HCID 6344Dichloromethane용매

실험 절차

(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate (1.45 g, 46.9 mmol) and triphenyl phosphite (5.00 mg, 0.0161 mmol) were dissolved in dichloromethane (12 mL). Ammonium metavanadate (50 mg, 0.427 mmol) and Pt/C (5% wt., 200 mg) were added and the reaction mixture was stirred under hydrogen (80 psi) for 5 h. The reaction mixture was filtered through a small plug of celite and the precipitate was washed multiple times with hot dichloromethane until it was free from white precipitate. The filtrate was concentrated in vacuo and crystallized with ethyl ether (15 mL). The resulting solid was filtered off and dried in vacuum to afford the title compound as an off-white solid (0.930 g, 80%). [M+H] calc'd for C12H13N3O3, 248; found, 248.

후처리

  1. filtrationThe reaction mixture was filtered through a small plug of celite
  2. washthe precipitate was washed multiple times with hot dichloromethane until it
  3. concentrationThe filtrate was concentrated in vacuo
  4. customcrystallized with ethyl ether (15 mL)
  5. filtrationThe resulting solid was filtered off
  6. customdried in vacuum

출처 및 근거

ORD 기록
ord-247b43cbca6648b286ea4c6d977fb310
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822470B2

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