Norprostol → Methyl 3-hydroxy-2-(3-hydroxy-3-methyl-1-octynyl)-5-oxocyclopentaneheptanoate

HRID 918273

Reaktionsgleichung

Reaktionsgleichung von HRID 918273
OC1CC(=O)C(CCCCCCC(OC)=O)=C1.CC(OC1CCCCO1)(CCCCC)C#C[Al](C#CC(OC1CCCCO1)(C)CCCCC)C#CC(OC1CCCCO1)(C)CCCCC.[Ga].[B].[OH:69][CH:70]1[CH2:74][C:73](=[O:75])[CH:72]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][C:82]([O:84][CH3:85])=[O:83])[CH:71]1[C:86]#[C:87][C:88]([CH3:101])([O:94]C1CCCCO1)[CH2:89][CH2:90][CH2:91][CH2:92][CH3:93]>C(O)(=O)C>[OH:69][CH:70]1[CH2:74][C:73](=[O:75])[CH:72]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][C:82]([O:84][CH3:85])=[O:83])[CH:71]1[C:86]#[C:87][C:88]([OH:94])([CH3:101])[CH2:89][CH2:90][CH2:91][CH2:92][CH3:93]

Komponenten

7

Edukt 5

HCID 3912664NorprostolHCID 5360835GalliumHCID 5462311BoronHCID 21521708Methyl 3-hydroxy-2-(3-methyl-3-[tetrahydropyran-2-yl]oxy-1-octynyl)-5-oxocyclopentaneheptanoateHCID 86733734Tri(3methyl-3-[tetrahydropyran-2-yl]oxy-1-octynyl) aluminum

Produkt 1

HCID 21521703Methyl 3-hydroxy-2-(3-hydroxy-3-methyl-1-octynyl)-5-oxocyclopentaneheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The 3-hydroxy-3-alkylated acetylenic compounds of this invention are prepared by employing the appropriately alkylated alkynyl boron, alkynyl gallium or alkynyl aluminum reactant. For example, treatment of methyl 3-hydroxy-5-oxocyclopent-1-eneheptanoate with tri(3methyl-3-[tetrahydropyran-2-yl]oxy-1-octynyl) aluminum, gallium or boron affords the epimeric methyl 3-hydroxy-2-(3-methyl-3-[tetrahydropyran-2-yl]oxy-1-octynyl)-5-oxocyclopentaneheptanoate. Typically, that compound may be hydrolyzed with a hydrolyzing agent such as hydrolytic acid, e.g. aqueous acetic acid, to yield the instant methyl 3-hydroxy-2-(3-hydroxy-3-methyl-1-octynyl)-5-oxocyclopentaneheptanoate.

Quellen und Nachweise

ORD-Eintrag
ord-fbc0dba1edb14fd3a2d083c0adf212e0
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03970683

Verknüpfte Notizen

Wird geladen…