Benzyl Alcohol → 1-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 2-benzylquinuclidin-3-yl ester

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In a mixture of sodium benzyl alkoxide prepared from 0.19 g of benzyl alcohol and 0.04 g of metallic sodium with 15 ml of toluene and 0.75 ml of DMF, 1.33 g of (R)-quinuclidin-3-ol was allowed to react with 3.00 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester for 8 hours while evaporating the solvents, thereby obtaining 1.38 g of 1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 2-benzylquinuclidin-3-yl ester (to be referred to as “compound F” hereinafter).

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