Ethanol → HCID 68824202, compound

Participants

Reaction Steps

Into a cooled (−78° C.) solution of 4-methoxycarbonylmethylene-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester (1.8 g, 6.4 mmol) in tetrahydrofuran (50 mL) obtained in the above 1) was slowly dropped, under an atmosphere of argon, 1 M diisobutylaluminum hydride in toluene (15.9 mL, 15.9 mmol). After dropping, the reaction mixture was stirred for 2 hours at the same temperature. After the reaction was completed, ethanol (10 mL) was added 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 (50 mL), and stirred for 30 minutes. After stirring, the reaction mixture was extracted with ether, and dried over anhydrous sodium sulfate. After drying, the extract was filtered and 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 0.95 g (yield 58.6%) of 4-(2-hydroxyethylidene)-3,3-dimethylpiperidine-1-carboxylic acid t-butyl ester. Its physical property is shown below.

Provenance & Evidence