Tetrahydrofuran → HCID 22859584, compound

Participants

Reaction Steps

A solution of 5-(3-MethoxycarbonyI-2-pyridyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole (393 mg, 1.073 mmol) (see Example 62) in tetrahydrofuran (2.5 ml) was added dropwise, with stirring, to a flask containing a solution of lithium aluminium hydride in tetrahydrofuran (35.9 mg of LiAIH4 in 10.0 ml THF) under a nitrogen atmosphere. The reaction was stirred for 24 hours whereupon the reaction mixture was quenched with aqueous sodium carbonate and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.7), to afford, after combination and evaporation of the appropriate fractions, the title compound as a white foam (298 mg). Found: C,71.55; H,6.93; N,12.20. C20H22N3O.1/5CH2Cl2 requires: C,71.70; H,6.97; N,12.42%.

Provenance & Evidence