Isopropyl iodide → Quinolizidin-2-ylmethyl-1-isopropylindole-3-carboxylate

Participants

Reaction Steps

A solution of eq-quinolizidin-2-ylmethylindole-3-carboxylate (E9b) (320 mg, 1.08 mmole) in dry THF (15 ml) at room temperature under nitrogen was treated with potassium t-butoxide (125 mg, 1.1 mmole) and stirred for 20 minutes. The solution was then treated with 2-iodopropane (0.11 ml, 1.1 mmole) and stirred for 18 h. The reaction mixture was treated with 10% Na2CO3 solution (25 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting initially with ether, then with ethyl acetate, to afford the title compound (E18) as a colourless oil (240 mg, 63%). This was converted to the hydrochloride salt mp 235°-238° C. (acetone).

Provenance & Evidence