(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine → (2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-1-[N-(phenoxy-acetyl)-L-prolyl]pyrrolidine

Participants

Reaction Steps

(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine (658 mg) was dissolved in 4N hydrochloric acid/1,4-dioxane (8 ml), and the mixture was stirred at room temperature for 0.5 hour. The residue obtained by concentration and drying of the reaction mixture was dissolved in methylene chloride (10 ml), and thereto were added dropwise triethylamine (0.42 ml) and phenoxyacetyl chloride (0.21 ml) under ice-cooling. After stirring the mixture under ice-cooling for 0.5 hour, and then at room temperature for 2 hours, the reaction mixture was treated in the same manner as in Example 46-D) to give 531 mg of the title compound.

Provenance & Evidence