Methanol → HCID 70445968, compound

Participants

Reaction Steps

A solution of 16.77 g (0.0557 mole) of 1-(phenylmethyl)-3-(phenylsulfonyl)pyrrolidine (free base) and 12.0 g (0.076 mole) of phenyl chloroformate in 500 ml of methylene chloride was stirred at room temperature for 4 hr. The solvent was removed in vacuo to give an oil. The oil was dissolved in ether with a little methyl alcohol and methylene chloride added to clear the solution. An excess of triethylamine was added and the solution stirred for 1 hr. The mixture was filtered and the solvent removed in vacuo from the filtrate to give an oil. This oil was suspended in 300 ml of 48% hydrobromic acid and the mixture was refluxed for 14.5 hr. The reaction mixture was extracted with several portions of ether and the ether layers discarded. The solution was made basic with 50% aqueous sodium hydroxide and the basic solution was extracted with several portions of methylene chloride. The combined methylene chloride extract of the basic solution was dried over magnesium sulfate and the solvent removed in vacuo to give an oil, the free base of the title compound. The free base was converted to the maleate salt, crystallizing and recrystallizing from methyl alcohol-diethyl ether to give 10.53 g (57.8%) of crystalline solid, m.p. 146.5°-147.5° C.

Provenance & Evidence