HCID 23150770, compound → HCID 11978506, compound

Participants

Reaction Steps

A suspension of platinum dioxide (300 mg) in a solution of trans-1-{3-[3-(4-fluorophenyl)allyloxy]propyl}pyrrolidine (330 mg) in N,N-dimethylformamide (3 mL) is stirred overnight at room temperature under an atmosphere of dihydrogene. An additional amount of platinum dioxide is added and the suspension is stirred for 24 hours at room temperature under an atmosphere of dihydrogene. The suspension is filtered over a celite pad and rinsed with ethyl acetate. Ethyl acetate is evaporated from the filtrate, platinum hydroxide (190 mg) is added and the suspension is stirred for 48 hours at room temperature under an atmosphere of dihydrogene. The suspension is filtered over a celite pad, rinsed with ethyl acetate, concentrated under reduced pressure and dissolved in a mixture of ethanol (2 mL) and diethyl oxide (200 μL). A solution of oxalic acid (58 mg) in ethanol (2 mL) is added. The mixture is concentrated under reduced pressure and suspended in diethyl oxide. The precipitate is filtered, rinsed with diethyl ether, dissolved in water (5 mL). The aqueous layer is made alkaline with ammonia and extracted twice with diethyl oxide (10 mL). The organic extracts are pooled, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol/ammonia from 99/10/0.1 to 92/2/0.2. Fractions containing the expected product are pooled, concentrated under reduced pressure, dissolved in diethyl oxide (2 mL). A solution of oxalic acid (21 mg) in acetone is added and the precipitate that appears is filtered and dried under reduced pressure at 40° C. under a film of diethyl oxide to give 96 mg of 1-{3-[3-(4-fluorophenyl)propoxy]propyl}pyrrolidine, oxalate as a white solid melting at 106° C.

Provenance & Evidence