Water → HCID 67460894, compound

Participants

Reaction Steps

A solution of (S)-1-[(R)-2-hydroxy-1-phenylethyl]-6-oxopiperidine-2-carbonitrile (400 mg) that is a known compound described in a document (see European Journal of Organic Chemistry, 2004, vol. 23, p. 4823-4829) in saturated hydrochloric acid-ethanol (7 mL) was stirred at room temperature for two days. A saturated sodium bicarbonate solution and chloroform were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 452 mg of a crude ester compound. Sodium borohydride (440 mg) was added to a solution of the resulting crude ester compound (452 mg) in methanol (10 mL) under ice-cooling, and the reaction solution was stirred at 0° C. for one hour and 50 minutes and then at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 166 mg of a diol compound. Triethylamine (145 μL) and p-toluenesulfonyl chloride (99.1 mg) were added to a solution of the resulting diol compound (108 mg) in methylene chloride (4.0 mL) under ice-cooling, and the reaction solution was stirred at room temperature overnight. The reaction solution was added dropwise to a solution of potassium tert-butoxide (97.2 mg) in THF (4.0 mL) under ice-cooling. Then, potassium tert-butoxide (194 mg) was added to the reaction solution, which was then stirred at room temperature for three hours and 40 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 23.3 mg of the title compound. The property values of the compound are as follows.

Provenance & Evidence