Potassium Carbonate → 1,2,3,4-Tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-yl methylcarbamate

Participants

Reaction Steps

To a solution of 1,2,3,4-tetrahydro-2-hydroxymethyl-4-methylcyclopent[b]indol-7-ol (1.7 g, 0.008 mole) in 50 ml of tetrahydrofuran was added milled K2CO3 (2.0 g, 0.015 mole), followed by a solution of methylisocyanate (0.5 ml, 0.008 mole) in 5 ml of tetrahydrofuran. After stirring at ambient temperature for two hours, the mixture was filtered and the filtrate concentrated to a yellow solid. This material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:2) via HPLC. The desired fractions were combined and concentrated to a white solid, 2.1 g, m.p. 134°-8° C. This material was recrystallized from methanol/ether (1:10) to give the product as a white solid, 1.5 g, m.p. 137°-8° C.

Provenance & Evidence