N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine → 1-Benzenesulfonyl-3-(2-dimethylamino-ethyl)-1H-indol-5-ol

HRID 635386ノート

反応式

HRID 635386 の反応式
[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]CC3C=CC=CC=3)[CH:13]=2)[N:8]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:7]=1)[CH3:3]>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH:7]=1)[CH3:3]

参加物

4

反応物 1

HCID 11729763N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine

生成物 1

HCID 98410771-Benzenesulfonyl-3-(2-dimethylamino-ethyl)-1H-indol-5-ol

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

A solution of N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine (2.25 g, 4.6 mmol) in absolute ethanol (100 ml) was hydrogenated at 40 psi over 20% palladium hydroxide (600 mg) for 4.5 h. Additional catalyst (1.6 g) was then added and hydrogenation was resumed at 45 psi for 2.5 h. The catalyst was removed by filtration, washed with a mixture of dichloromethane-methanol-ammonia (80:20:2; 3×70 ml), and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography (silica gel, dichloromethane-methanol-ammonia, 95:5:0.5) to give the title compound as a crystalline solid after trituration with diethyl ether (30 ml); mp 185°-188° C.; δH (360 MHz, DMSO-d6) 9.32 (1H, br s), 7.90-7.84 (2H, m), 7.69 (1H, d, J=8.7 Hz), 7.68-7.62 (1H, m), 7.55 (2H, t, J=8.0 Hz), 7.48 (1H, s), 6.82 (1H, d, J=2.2 Hz), 6.78 (1H, dd, H=8.8 and 2.2 Hz), 2.67 (2H, t, J=7.6 Hz), 2.47 (2H, t, J=7.6 Hz), 2.18 (6H, s); m/z (ES) 345 (M++1). (Found: C, 62.91; H, 5.86; N, 8.16. C18H20N2O3 requires: C, 62.77; H, 5.85; N, 8.13%).

後処理

  1. customThe catalyst was removed by filtration
  2. washwashed with a mixture of dichloromethane-methanol-ammonia (80:20:2; 3×70 ml)
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica gel, dichloromethane-methanol-ammonia, 95:5:0.5)

出典と根拠

ORDレコード
ord-ee6daca5bc9c4f72aee5ea56ef00dad8
出典データセット
uspto-grants-2001_02
特許番号
US06187805B1

反応ノート

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