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0 °C

A solution of 1-{4-[2-(2-methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (300 mg) and dry tetrahydrofuran (15 ml) was cooled to 0° C., and lithium aluminum hydride (46 mg) was added. The reaction mixture was maintained at 0° C. for 1 hour, and then was quenched by adding 1N hydrochloric acid. The resulting mixture was filtered through a bed of celite, diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated. Purification of the residue by column chromatography (silica gel, 15 g; ethyl acetate-n-hexane, 1:2) gave 1-{4-[2-(2-hydroxymethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (80 mg) as a amorphous.

1. customwas quenched
2. additionby adding 1N hydrochloric acid
3. filtrationThe resulting mixture was filtered through a bed of celite
4. additiondiluted with ethyl acetate
5. washwashed with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customPurification of the residue by column chromatography (silica gel, 15 g; ethyl acetate-n-hexane, 1:2)