Acrylic Acid → 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic Acid

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with biphenyl-2-ylcarbamic acid piperidin-4-yl ester (50 g, 67.6 mmol, 1 equiv.; prepared as described in Preparation 1) and 500 mL of DCM. Acrylic acid (15.05 mL, 100 mmol, 1.3 equiv.) was added and the reaction was heated to 50° C. (reflux) for 18 hours. The DCM was removed in vacuo and MeOH (600 mL) was added. The MeOH solution was heated to 75° C. for 2 hours then allowed to cool to room temperature, during which time a thick slurry formed. The precipitate was collected via vacuum filtration, washed with MeOH (50 mL), and dried on the filter to afford 61 g of the title intermediate (98% yield).

Provenance & Evidence