Tetrahydrofuran → 5-(methyloxy)-1-(1-methyl-L-prolyl)-2,3-dihydro-1H-indol-6-amine

HRID 1014285노트

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HRID 1014285 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([C:15](=[O:22])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21])[CH2:7][CH2:6]2.O1CCCC1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([C:15](=[O:22])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21])[CH2:7][CH2:6]2

참가 물질

5

반응물 2

HCID 8028TetrahydrofuranHCID 673158805-(methyloxy)-1-(1-methyl-L-prolyl)-6-nitro-2,3-dihydro-1H-indole

생성물 1

HCID 673161895-(methyloxy)-1-(1-methyl-L-prolyl)-2,3-dihydro-1H-indol-6-amine수율 99%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
65 °C

실험 절차

A suspension of 5-(methyloxy)-1-(1-methyl-L-prolyl)-6-nitro-2,3-dihydro-1H-indole (2.50 g, 8.19 mmol) in methanol (100 mL)/tetrahydrofuran (100 mL) was warmed to 65° C. and maintained until all solids had dissolved. The solution was cooled, purged with nitrogen for 40 minutes, and 10% palladium on carbon (1.1 g, 8.19 mmol) was added and the suspension was maintained under 40 psi of H2 gas with rapid stirring for 24 hours. The solution was carefully purged with nitrogen, filtered through a pad of celite, and all solvents removed under reduced pressure to afford 5-(methyloxy)-1-(1-methyl-L-prolyl)-2,3-dihydro-1H-indol-6-amine (2.23 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.57 (s, 1 H), 6.70 (s, 1 H), 4.76 (s, 2 H), 4.06-4.17 (m, 1 H), 3.93-4.06 (m, 1 H), 3.70 (s, 3 H), 3.46 (s, 1 H), 3.06-3.18 (m, 1 H), 2.98 (t, J=8.25 Hz, 2 H), 2.41-2.47 (m, 1 H), 2.37 (s, 3 H), 2.12-2.29 (m, 1 H), 1.66-1.92 (m, 3 H).

후처리

  1. temperaturemaintained until all solids
  2. dissolutionhad dissolved
  3. temperatureThe solution was cooled
  4. custompurged with nitrogen for 40 minutes
  5. temperaturethe suspension was maintained under 40 psi of H2 gas
  6. customThe solution was carefully purged with nitrogen
  7. filtrationfiltered through a pad of celite
  8. customall solvents removed under reduced pressure

출처 및 근거

ORD 기록
ord-88087500b10647649abfdf3e5e668a13
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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