Phosphoric Acid → tert-butyl 4-(4-ethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Add palladium hydroxide on carbon (4.20 g, 60% wet, 0.15 g/g limiting reagent) to a solution of tert-butyl 4-(4-(1-hydroxyethyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate; phosphoric acid (28.00 g, 57.08 mmol) in methanol (10 mL). Stir under a hydrogen atmosphere in a Parr system (150 psi, 60° C.) for six days. Stir further under a hydrogen atmosphere in a Parr system (300 psi, 80° C.) for seven days. Filter over Celite®. Concentrate the filtrate in vacuo and dilute with acetone (280 mL). Stir overnight at room temperature. Filter and dry the resulting white solid under vacuum to give tert-butyl 4-(4-ethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate; phosphoric acid (23.00 g, 85%). MS (ES) m/z=377 [M]+.

Provenance & Evidence