Acetyl chloride → a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As shown in Scheme IV, in this method, adamantyl bromide (Formula A) is alkylated via zinc chloride catalysis to produce <a-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B). <a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula B) is then esterified using acetyl chloride in methanol to produce <a-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C). <a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula C) is then converted to <a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) by Swern oxidation. <a-Oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula D) is then hydroxylated to form 3-hydroxy-<a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester (Formula I), which is then hydrolyzed to form 3-hydroxy-<a-oxotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula II). Also see Examples 21 through 25 herein.
Sources & evidence
- ORD record
- ord-e8ed3d90d1614a86b9373aa692b72df5
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420079B2
Reaction notes
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