Acetyl chloride → a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester

HRID 1514022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514022
[OH:1][CH:2]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)[C:3]([OH:5])=[O:4].[C:16](Cl)(=O)C>CO>[OH:1][CH:2]([C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2)[C:3]([O:5][CH3:16])=[O:4]

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 3543000alpha-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Produkt 1

HCID 10922162a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

As shown in Scheme II, in this method, adamantyl bromide (Formula A) is alkylated via zinc chloride catalysis to produce α-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B). α-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B) is then esterified using acetyl chloride in methanol to produce α-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C). α-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C) is then converted to α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) by Swern oxidation. α-Oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) is then hydroxylated to form 3-hydroxy-α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula 1a), which is then hydrolyzed to form 3-hydroxy-α-oxotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula 1).

Quellen und Nachweise

ORD-Eintrag
ord-51d520debec646b8932c9f6e36cb9623
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222009B2

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