Acetic Acid → 1,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid

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Reaction Conditions

Reaction Steps

To 100 ml of 80% acetic acid in water, was added 1,2,3,4-tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester (10 g, 0.03 mole). After stirring at 100° C. for four hours, the mixture was cooled, poured into 500 ml of water, stirred for five minutes, and extracted with ethyl acetate (3×). The organic layer was washed successively with water and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~10 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to a tan solid, 1.3 g, m.p. 160°-162° C. This material was recrystallized from ether to give the product as a tan solid, 1.0 g, m.p. 161°-163° C.

Provenance & Evidence