methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylate → methyl 5-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}-1H-indole-2-carboxylate

HRID 722772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722772
[NH2:1][C@H:2]([CH3:17])[CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]2.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:33]Br)=[CH:28][C:27]=1[CH2:43][OH:44])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[NH3:1].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([O:35][Si:36]([C:39]([CH3:41])([CH3:40])[CH3:42])([CH3:37])[CH3:38])[CH2:33][NH:1][C@H:2]([CH3:17])[CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7]3)=[CH:28][C:27]=1[CH2:43][OH:44])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 2

HCID 12988833methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylateHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol

Produkt 2

HCID 222AmmoniaHCID 12988832methyl 5-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}-1H-indole-2-carboxylateAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of methyl 5-[(2R)-2-aminopropyl]-1H-indole-2-carboxylate (Preparation 14, 5.00 g, 21.5 mmol) and [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl] oxy}ethyl)phenyl]methanol (Preparation 20, 4.86 g, 10.8 mmol) in dichloromethane (50 ml) was heated to 90° C. allowing the dichloromethane to evaporate gradually. The resulting melt was left at 90° C. for 16 h under nitrogen. The reaction mixture was then cooled to room temperature and the resulting solid triturated with dichloromethane. The solid was filtered off and the solvent removed in vacuo to give a pale orange oil. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (99:1:0.1 by volume) to give the title compound as a pale yellow oil (3.90 g).

Aufarbeitung

  1. customto evaporate gradually
  2. customthe resulting solid triturated with dichloromethane
  3. filtrationThe solid was filtered off
  4. customthe solvent removed in vacuo
  5. customto give a pale orange oil
  6. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8d7e2f8f1110428ca1b5435a9d166d43
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138527B2

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