Potassium Iodide → 2-Methyl-7-pyrrolidin-1-ylmethyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic Acid Benzyl Ester

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Reaction Steps

7-Bromomethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester (0.160 g, 0.390 mmol, 1 eq) was suspended in dry acetonitrile (10 mL) under Ar. Potassium iodide (catalytic) was added followed by the addition of pyrrolidine (0.125 mL, 1.50 mmol, 3.75 eq). The reaction mixture was stirred and heated to reflux. The reaction was followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 18 hours, the reaction was quenched with aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate /methanol/triethylamine 87/10/3. 0.063 g (40% yield) of the indole-pyrrolidine was obtained as a white solid. This was converted to the .HCl salt, LC/MS (ESI+) 405 (M+1), Anal. (C25H28N2O3.HCl.0.2 DMF) C, H, N.

Provenance & Evidence