Deuteration of α-sec-Butyl-p-Hydroxybenzyl Alcohol

It has been proved that α-sec-butyl-p-hydroxybenzyl alcohol (T-018) is a strong sedative and an ticonvulsant. Deuterated T-018 was prepared as a tracer for studying the metabolism of T-018. 2-Iodo-T-018 (2. 10 g), prepared by the iodination of T-018 using chloramine T, was dissolved in 70 ml methanol and,after the addition of 750 mg 5% Pd/C and 15 ml triethylamine,treated with deuterium gas for 9 h. A mixture of mono-and di-deuterated T-018 was obtained;yield was 84.77 %. Molecular clustering as determined by MS showed that the product consisted of dideutero-T-018 (m/e 182) and monodeutero-T-018 (m/e 181) in the ratio of 2.3: 1.