3-Hydroxyadamantane-1-carboxylic acid → 3-(Hydroxymethyl)adamantan-1-ol

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Reaction Steps

In an atmosphere of nitrogen, 15 mmole of lithium aluminium hydride was suspended into 15 mL of tetrahydrofurane (THF). To the resultant mixture was slowly added 10 mmole of 1-carboxy-3-adamantanol obtained by the method of Example 2 while keeping the temperature of the mixture at 10° C. or below by using an ice bath. After warming the mixture to room temperature, the mixture was refluxed for 16 hours. As a result, 1-hydroxymethyl-3-adamantanol (yield 95%) was obtained. The conversion of 1-carboxy-3-adamantanol was 99%.

Provenance & Evidence