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

HRID 1014285ノート

反応式

HRID 1014285 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-88087500b10647649abfdf3e5e668a13
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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