a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl ester → Methyl 2-(3-hydroxy1-adamantyl)-2-oxoacetate

HRID 17767Notes

Reaction equation

HRID 17767 reaction equation
[OH:1][CH:2]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2)[C:3]([O:5][CH3:6])=[O:4].[O:17]=C(C12CC3CC(CC(C3)C1)C2)C(OC)=O>>[OH:17][C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([C:2](=[O:1])[C:3]([O:5][CH3:6])=[O:4])([CH2:14]3)[CH2:8]1)[CH2:10]2

Participants

3

Reactant 2

HCID 10922162a-Hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid, methyl esterHCID 53353319Methyl 2-(1-adamantyl)-2-oxoacetate2×

Product 1

HCID 10331759Methyl 2-(3-hydroxy1-adamantyl)-2-oxoacetate

Procedure

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-I-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).

Sources & evidence

ORD record
ord-dccde9a852b542a8a54c784bf55597c7
Source dataset
uspto-grants-2010_06
Patent number
US07741082B2

Reaction notes

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