Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate → methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate

Participants

Reaction Steps

Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate (Intermediate 22, 0.650 g) was dissolved in a solution of hydrogen chloride in methanol (1.25M, 18 ml) and the resultant mixture was stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous potassium carbonate solution (10%). The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate (0.388 g) as a dark orange gum.

Provenance & Evidence