Vinylcyclopentane → (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one

HRID 1670415

Reaktionsgleichung

[OH:1][C@@H:2]1[C@H:6]([C@H:7]([OH:10])[CH:8]=[CH2:9])[O:5][C:4](=[O:11])[C@@H:3]1[O:12][CH3:13].C([CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[CH:16]1(/[CH:9]=[CH:8]/[C@H:7]([C@@H:6]2[O:5][C:4](=[O:11])[C@H:3]([O:12][CH3:13])[C@@H:2]2[OH:1])[OH:10])[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

100 mg (0.53 mmol) of 18, 4 ml of CH2Cl2, 726 μl (5.3 mmol) of vinylcyclopentane and then 90.2 mg (106 μmol) of second-generation Grubbs catalyst are introduced into a 5 ml vial. The solution is microwave-heated at 60° C. for 10 min. The solvent is subsequently evaporated to dryness under reduced pressure and the residue is then purified on a Biotage 12-M silica column (eluent: 40/60 Hept/EtOAc). The product 19 (76.3 mg, Rf=0.35 under the elution conditions used) is obtained in the form of a brown solid.

Aufarbeitung

customThe solvent is subsequently evaporated to dryness under reduced pressure
customthe residue is then purified on a Biotage 12-M silica column (eluent: 40/60 Hept/EtOAc)
washThe product 19 (76.3 mg, Rf=0.35 under the elution conditions
customis obtained in the form of a brown solid

Quellen und Nachweise

ORD-Eintrag: ord-5849822b29894a59bb8341c76a109f29
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07994162B2

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