Hydrochloric Acid → Hydrochloric Acid

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Reaction Steps

A solution of [3-(6-fluoro-indol-1-yl)-propyl]-[(2S)-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl]-amine (0.53 g, 1.3 mmol) in 1.05 mL of formaldehyde, 0.11 mL of acetic acid and 20 mL of methanol was added to 95% sodium cyanoborohydride (0.13 g, 1.9 mmole). The mixture was allowed to stir at room temperature under nitrogen overnight. The mixture was partitioned between 400 mL each of methylene chloride and water. The organic portion was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was then column chromatographed on silica gel using 55% ethyl acetate/44% hexane/1% methanol as eluant. The product-containing fractions were concentrated under vacuum to give a yellow oil, which was dissolved in ethyl acetate and treated with excess HCl in ether to give 0.040 g of the (S)-enantiomer of the title compound as a yellow hydrochloride, m.p. 75.9-83.7° C.

Provenance & Evidence