Sodium Bicarbonate → HCID 19067180, compound

Participants

Reaction Steps

1.80 g of 2-(2-benzyloxycarbonylethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 10 ml of ethanol, and 4.77 g of tin chloride dihydrate was added to the solution. The solution was heated under reflux with stirring for 30 minutes. The resulting solution was neutralized by adding saturated aqueous solution of sodium bicarbonate, and the solution was extracted with ethyl acetate, washed with water and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the residue was purified by silica gel column chromatography to obtain 1.52 g of 7-amino-2-(2-benzyloxycarbonylethyl)-1,2,3,4-tetrahydroisoquinoline as an oily product. This product, with no further purification, was dissolved in 10 ml of DMF, and 1.52 g of 1-(tertbutoxycarbonyl)-4-(carboxymethoxy)piperidine and 0.41 g of 1-ethyl-3-(3-dimethylaminopopyl)carbodiimide, which had been separately synthesized, were added to this solution. The solution was stirred overnight at room temperature. The resulting solution was extracted with ethyl acetate, washed with water, saturated aqueous solution of sodium bicarbonate, and saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the residue was purified by silica gel column chromatography to obtain 1.84 g of 2-(2-benzyloxycarbonylethyl)-7-[1-(tert-butoxycarbonyl)piperidine-4-yloxyacetylamino]-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 68%).

Provenance & Evidence