Triphenylphosphine → Triphenylphosphine Oxide

HRID 552728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552728
ClC1N=CN=C2C=1N=CN2[C@H]1[C@@H]2[O:16]C(C)(C)O[C@@H]2[C@@H](CO)C1.C(NS(=O)=O)(OC(C)(C)C)=O.[C:34]1([P:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CCOC(C)=O>[C:47]1([P:40](=[O:16])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10064860((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanolHCID 178454374HCID 178454374, Verbindung

Produkt 1

HCID 13097Triphenylphosphine Oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of ((3aR,4R,6R,6aS)-[6-(6-chloro-purin-9-yl)-2,2-dimethyltetrahydro-cyclopenta[1,3]dioxol-4-yl]-methanol (Yang, M.; Wei, Y.; Schneller, S. W. J. Org. Chem. 2004, 69, 3993-3996) (250.0 mg, 0.77 mmol), N-Boc-sulfonamide (226.6 mg, 1.16 mmol) and triphenylphosphine (242.3 mg, 0.92 mol) in EtOAc (8 mL) was added diisopropyl azodicarboxylate (227.3 μL, 1.16 mmol) dropwise as a solution in EtOAc (1 mL). The reaction was stirred at r.t. overnight, quenched with water and extracted with EtOAc. The organics were concentrated and the residue purified by flash chromatography (0 to 100% EtOAc/DCM) to obtain the product as an inseparable mixture with triphenylphosphine oxide. The material was carried on as such.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. concentrationThe organics were concentrated
  4. customthe residue purified by flash chromatography (0 to 100% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-92f5bc84dbc246fb9bdcb1900addf900
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951810B2

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