Triphenyl phosphite → (S)-3-bromo-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

HRID 2077959

반응식

HRID 2077959 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N+:18]([O-])=O)[C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13](OCC)=[O:14])=[N:6][CH:7]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[C:13](=[O:14])[NH:18][C:4]=2[CH:3]=1

참가 물질

6

반응물 2

HCID 7540Triphenyl phosphiteHCID 58324356(S)-ethyl 1-(5-bromo-3-nitropyridin-2-yl)pyrrolidine-2-carboxylate

생성물 1

HCID 58324379(S)-3-bromo-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one수율 42.8%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 516859Ammonium metavanadate촉매HCID 6344Dichloromethane용매

실험 절차

(S)-ethyl 1-(5-bromo-3-nitropyridin-2-yl)pyrrolidine-2-carboxylate (8.6 g, 24.99 mmol) was dissolved in dichloromethane (Volume: 125 ml) and to this solution was added triphenyl phosphite (0.078 g, 0.250 mmol), ammonium metavanadate (0.175 g, 1.499 mmol) and Pt/C (5% wt.) (0.975 g, 0.250 mmol). The reaction mixture was hydrogenated at 80 psi at 25° C. for 4 h. The reaction mixture was filtered through celite using DCM and MeOH to complete the transfer and wash the celite plug. The combined filtrates and washes were concentrated in vacuo and crystallized with ethyl ether (75 mL). The precipitate was filtered and dried in vacuum to afford (S)-3-bromo-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (2.87 g, 10.70 mmol, 42.8% yield) as a pale beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82-2.03 (m, 3H) 2.11-2.26 (m, 1H) 3.27-3.47 (m, 1H) 3.49-3.63 (m, 1H) 4.01-4.11 (m, 1H) 7.06

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washwash the celite plug
  3. concentrationThe combined filtrates and washes were concentrated in vacuo
  4. customcrystallized with ethyl ether (75 mL)
  5. filtrationThe precipitate was filtered
  6. customdried in vacuum

출처 및 근거

ORD 기록
ord-c46bab119ca84d56922f08f1b079ce98
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928105B2

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