Water → Ethyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-10-Carboxylate

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Reaction Steps

A solution of ethyl 2-(5-chlorovalerylamino)phenylacetate (8.10 g, 0.027 mole) in dry THF (50 ml) was added to a stirred suspension of potassium t-butoxide (7.62 g, 0.068 mole) in dry THF (200 ml) at room temperature under nitrogen. After 1 h the purple solution produced was treated with water (10 ml) and concentrated in vacuo. The residue was shaken with ethyl acetate (200 ml) and sat.ammonium chloride solution (150 ml), then the organic layer separated, dried (Na2SO4) and concentrated in vacuo to afford an orange oil. This was chromatographed on silica gel eluting with ether to afford the title compound as a yellow solid (1.25 g, 20%).

Provenance & Evidence