Hydrochloric Acid → HCID 23565291, compound

Participants

Reaction Conditions

Reaction Steps

1.1 ml of dibromomethane was dissolved in tetrahydrofuran (20 ml) and cooled to −90° C. Into the solution thus obtained were dropped 9.77 ml of a 1.6 M solution of n-butyllithium in hexane and 20 ml of a solution of lithium 2,2,6,6-tetramethylpiperidide, which had been prepared from 2.88 ml of 2,2,6,6-tetramethylpiperidine, in tetrahydrofuran while maintaining the bulk temperature at 10° C. or below. 5 minutes thereafter, 10 ml of a solution of 1.0 g of ethyl (3-methyl-3-azabicyclo[3.3.1]non-1-yl)carboxylate in tetrahydrofuran was dropped thereinto. After 20 minutes, 0.8 ml of 2,2,6,6-tetramethylpiperidine was added thereto. 5 minutes thereafter, 23.7 ml of a 1.6 M solution of n-butyllithium in hexane was dropped thereinto and the resulting mixture was stirred. After 10 minutes, the reaction mixture was heated to 30° C. and stirred for 1 hour. Then the reaction mixture was quickly dropped into a solution of hydrogen chloride prepared from 25 ml of acetyl chloride and 250 ml of ethanol and stirred at room temperature for 14 hours. The reaction mixture was concentrated and an aqueous solution of potassium carbonate was added thereto followed by the extraction with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.63 g of the title compound as a slightly yellow oily substance.

Provenance & Evidence