Diisopropylethylamine → (1-(9-(1,3-Dioxolan-2-yl)nonyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

Participants

Reaction Conditions

Reaction Steps

2-(8-Bromooctyl)-1,3-dioxolane (218 mg, 0.82 mmol) followed by di-isopropylethylamine (361 μL, 2.07 mmol) were added to a solution of piperidin-4-ylmethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride (252 mg, 0.69 mmol) in acetonitrile (4 mL). The reaction mixture was heated at 60° C. for 17 hours. After this time, the reaction was cooled to RT and diluted with dichloromethane. The organic extracts were washed with water, filtered through a hydrophobic frit, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 100% dichloromethane to 40:1 dichloromethane:methanol to afford the title compound that was used without further purification in the next step.

Provenance & Evidence