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

HRID 1351936노트

반응식

HRID 1351936 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-6f6f286a711e44f0a28666cc9f324937
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217724B2

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