(R)-(+)-3-Chlorostyrene oxide → HCID 69455783, compound

HRID 1351955Notes

Reaction equation

HRID 1351955 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:15][C@H:16]([NH2:18])[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[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:14]=[C:13]2[C:9]([C:10]([CH2:15][C@H:16]([NH:18][CH2:26][C@@H:25]([C:24]3[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=3)[OH:27])[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:20]

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69458689HCID 69458689, compound

Product 1

HCID 69455783HCID 69455783, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-3-(2-aminopropyl)-1H-indole-6-carboxylic acid diethylamide (960 mg, 3.51 mmol) in acetonitrile (10 ml) is added (R)-(+)-3-chlorostyrene oxide (1.09 g, 7.02 mmol), and the mixture is refluxed for 5 hours. The reaction solution is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (chloroform/methanol=20/1→(a saturated ammonia solution in chloroform)/methanol=20/1) to give 3-{(2R)-2-[2-(3-chloro-phenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-6-carboxylic acid diethylamide (950 mg, 2.22 mmol, 63%).

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (chloroform/methanol=20/1→(a saturated ammonia solution in chloroform)/methanol=20/1)

Sources & evidence

ORD record
ord-4cf914ad7800417a816af4dd4a17a015
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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