(R)-(+)-3-Chlorostyrene oxide → 3-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide

HRID 1351936ノート

反応式

HRID 1351936 の反応式
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH2:18])[CH3:17])=[O:5])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C@H:25]1[O:27][CH2:26]1>C(#N)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:26][C@@H:25]([C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=1)[OH:27])[CH3:17])=[O:5])[CH3:20]

参加物

4

反応物 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69457261(R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide

生成物 1

HCID 694562293-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide収率 39%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of (R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide (1.30 g, 4.76 mmol) and (R)-(+)-3-chlorostyrene oxide (1.21 mL, 9.52 mmol) in acetonitrile (15 mL) is refluxed for 10 hours. After cooling, the mixture is concentrated and the residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform) to give the desired 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid diethylamide (0.79 g, yield: 39%).

後処理

  1. temperatureis refluxed for 10 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customthe residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform)

出典と根拠

ORDレコード
ord-6f6f286a711e44f0a28666cc9f324937
出典データセット
uspto-grants-2007_05
特許番号
US07217724B2

反応ノート

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