Hydrochloric Acid → HCID 66625010, compound

Participants

Reaction Conditions

Reaction Steps

[Step 2] 715 mg of 1-acetyl-2-methyl-4-[(4-tert-butyldiphenylsilyloxymethylphe nyl)imino]-1,2,3,4-tetrahydroquinoline, 74 mg of sodium borohydride, and 488 mg of cerium trichloride heptahydrate were dissolved in 8 mL of methanol, and the solution was stirred for 2 hours at 50° C. After completion of the reaction, 1 N hydrochloric acid was added to the reaction liquid, and the mixture was stirred for 30 minutes. The reaction liquid was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and then was extracted with chloroform. The organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine, dehydrated with anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (hexane:ethyl acetate=1:1), and thus 615 mg (85%) of 1-acetyl-4-[(4-tert-butyldiphenylsilyloxymethylphenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a yellow oily substance (cis:trans=3:1).

Provenance & Evidence