1,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol → 1,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-ol

Participants

Reaction Steps

To a suspension of 10% Pd/C (1.2 g) in 50 ml of ethanol was added a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methylcyclopent[b]indole-2-methanol (8.4 g, 0.027 mole) in 200 ml of ethanol in a Parr hydrogenation bottle. After shaking at 50° C., under 50 psi hydrogen for two hours, the mixture was cooled, filtered, and then concentrated to a dark oil. The oil was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC. The desired fractions were combined and then concentrated to a light yellow solid. The material was triturated with ether and dried to give 4.0 g (66%) of the product as an off-white solid, m.p. 153°-4° C.

Provenance & Evidence