1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 71245714, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-hydroxy-2-phenyl-2-(thiophen-3-yl)acetic acid (0.75 g, 3.197 mmol) in toluene (4 mL) and dimethyl formamide (0.4 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (735 μL, 4.919 mmol) was added followed by tert-butyl 4-(tosyloxymethyl)piperidine-1-carboxylate (0.909 g, 2.459 mmol) in toluene (3.5 ml) and dimethyl formamide (0.35 mL). The reaction mixture was heated at 100° C. overnight. After this time, the reaction mixture was cooled to RT and concentrated in vacuo. The crude mixture purified by silica gel column chromatography eluting with a gradient of iso-hexane:ethyl acetate (1:0 to 3:1) to afford the title compound (0.84 g, 79%).

Provenance & Evidence