Benzyl Alcohol → HCID 58671545, compound

Participants

Reaction Steps

A solution of compound 5F (0.083 g, 0.207 mmol) in 1.5 mL of 1:2 TFA/dichloromethane) was stirred at room temperature for 3 h, evaporated under reduced pressure and re-evaporated from carbon tetrachloride. The yellow oil was dissolved in ethyl acetate, washed with 10% citric acid and the aqueous layer re-extracted with EtOAc. The organic extracts were combined, dried (MgSO4) and evaporated to give a yellow semi-solid. The solid was treated with saturated sodium bicarbonate solution and then brought to pH 6 with 1 M hydrochloric acid. The aqueous phase was extracted twice with EtOAc. The extracts were combined, dried (MgSO4), filtered and evaporated to give a yellow solid. This solid was slurried in 1.0 mL of dioxane and DPPA (0.031 mL, 0.144 mmol), triethylamine (0.021 mL, 0.151 mmol) and benzyl alcohol (0.015 mL, 0.145 mmol) were added. After 20 min at room temperature, the mixture was heated to reflux for 15 h. The resulting deep red solution was cooled, diluted with EtOAc, washed once with saturated sodium bicarbonate solution, dried (MgSO4), filtered and evaporated. Purification by silica gel chromatography (7:93 Ether/CH2Cl2) provided the title compound benzyl 8-benzyl-3-phenyl-5,6,7,8-tetrahydropyrido[2,3-c]pyridazin-6-ylcarbamate as a red solid (0.024 g, 44%). MS [M+H]+: found 451.

Provenance & Evidence