trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine → Rac-(3r,4r)-4-phenoxypyrrolidin-3-ol

Participants

Reaction Steps

1.77 g (0.005 mol) of the resulting trans-3-hydroxy-4-phenoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine are dissolved in 20 ml of 90% strength acetic acid and the solution is treated at 0° with 2 g of zinc dust in portions. The reaction mixture is then stirred at room temperature for one hour and filtered through a layer of diatomaceous earth and the filtrate is rendered alkaline with concentrated sodium hydroxide solution and extracted 3 times with ether. The organic phase is washed with water, dried over calcium chloride and evaporated under a water pump vacuum, and trans-3-hydroxy-4-phenoxy-pyrrolidine is obtained in the form of the crude base, which crystallises from methylene chloride/hexane; melting point 120°-122°. The neutral fumarate of this compound, which has a melting point of 144°-146°, is obtained by reaction with a solution of fumaric acid in methanol/ether.

Provenance & Evidence