[CH3:1][C:2]12[CH2:12][C:6]3([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4](C(O)=O)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:17]([OH:20])(=O)[CH3:18].S(Cl)([Cl:23])=O>CO.CCOC(C)=O.[Pd]>[CH3:1][C:2]12[CH2:12][C:6]3([CH3:13])[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([CH2:18][C:17]([Cl:23])=[O:20])([CH2:5]3)[CH2:3]1)[CH2:9]23,5,7-trimethyl adamantane-1-carboxylic acid was converted to it's acid chloride per the procedure described for 3,5-dimethyl-adamantan-1-yl)-acetic acid. It was then homologated to the corresponding benzyl ester via the procedure described in Tetrahedron Letters, 1980, 21, 4461-4462. The benzyl ester was converted to the acid by standard hydrogenation conditions of 10% Pd/C in MeOH/EtOAc::1:1. The acid was then converted to the acid chloride via standard treatment with thionyl chloride at reflux for 1 to 2 hours. Excess reagent was azeotropically removed with hexanes and the resulting acid chloride was used without further purification.
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