(S)-(+)-2-(Methoxymethyl)pyrrolidine → 1H-Indolamine

Participants

Reaction Steps

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.350 g, 0.900 mmol, 1 eq, Example 56, Step D) was suspended in dioxane (20 mL) under Ar. (S)-2-(Methoxymethyl)-pyrrolidine (0.207 g, 1.800 mmol, 2 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). 0.200 g (55%) of the indole-amine was obtained as a white solid. This was converted to the HCl salt. LC/MS (ESI+) 407 (M+1); Anal. Calcd for C25H30N2O3.1HCl.1H2O: C, 65.14; H, 7.22; N, 6.08; Found: C, 65.48; H, 7.14; N, 6.04.

Provenance & Evidence