Triphenylphosphine → 9-((1R,4S)-4-Hydroxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

HRID 215884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 215884
[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][NH:11]2)=[C:7]([NH:14][C@H:15]([CH2:23][OH:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]=1)=[O:4].[H-].[Na+].[OH:27][C@@H:28]1[CH2:32][CH2:31][C@H:30](OC(=O)C)[CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:31]2[CH2:32][C@H:28]([OH:27])[CH:29]=[CH:30]2)=[C:7]([NH:14][C@H:15]([CH2:23][OH:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 15407440(1S,3R)-3-Hydroxycyclopentyl acetateHCID 178499116HCID 178499116, Verbindung

Produkt 1

HCID 670229569-((1R,4S)-4-Hydroxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

6-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (1.05 eq.) is suspended in THF (deoxygenated & dry). NaH (1.05 eq.) is added over 5 minutes and the reaction mixture is stirred at RT over 30 minutes. A solution of acetic acid (1S,3R)-3-hydroxy-cyclopentyl ester (1 eq.), triphenylphosphane (0.15 eq.) and tris(dibenzylideneacetone)dipalladium(0) in THF (deoxygenated & dry) is added to reaction. The reaction mixture is reflux for 6 hours. The reaction mixture is reduce in vacuo and columned to give the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture is reflux for 6 hours

Quellen und Nachweise

ORD-Eintrag
ord-56c23c62e5ae44b58fae5832e3689b08
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193164B2

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