1,3,3-Trimethyl-6-azabicyclo(3.2.1)octane → 1H-Indolamine

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Reaction Steps

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.200 g, 0.510 mmol, 1 eq, Example 56, Step D) was suspended in dioxane (30 mL) under Ar. 1,3,3-trimethyl-6-azabicyclo-[3,2,1]octane (0.235 g, 1.540 mmol, 3 eq) was added. The reaction mixture was stirred and heated to reflux for 18 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases 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/triethyl amine (100/10/1). 0.123 g (54%) of the indole-amine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 446 (M+1); Anal. Calcd for C29H36N2O2.1HCl.1.25H2O: C, 68.55; H, 7.93; N, 5.51; Found: C, 68.66; H, 7.54; N, 5.41.

Provenance & Evidence