Ethanol → HCID 68826072, compound

Participants

Reaction Steps

A solution of 1 M diisobutylaluminum hydride in toluene (13.9 mL, 13.9 mmol) was slowly dropped into a cooled (-78° C.) solution of 4-methoxycarbonylmethylene-3-methylpiperidine-1-carboxylic acid t-butyl ester (1.5 g, 5.6 mmol) obtained in the above 1) in tetrahydrofuran (30 mL) under an atmosphere of argon. After dropping, it was stirred for 2 hours at the same temperature. After the reaction was completed, ethanol (8 mL) was added thereto at 0° C. and allowed to warm to room temperature gradually. The reaction mixture was then concentrated under a reduced pressure, treated with an aqueous solution of 20% sodium potassium tartrate (20 mL), and stirred for 30 minutes. After stirring, the solution was extracted with ether, dried over anhydrous sodium sulfate. After drying, it was filtered, and the filtrate was concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1) to obtain 1.2 g (yield 89.6%) of 4-(2-hydroxyethylidene)-3-methylpiperidine-1-carboxylic acid t-butyl ester. Its physical property is shown below.

Provenance & Evidence