Reaktion #1807712

Reaktionsgleichung

triethylamine

(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine

phenoxyacetyl chloride

→

title compound

(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-[N-(phenoxyacetyl)-L-prolyl]pyrrolidin

Lösungsmittel

methylene chloride

hydrochloric acid 1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated to dryness
2. 2
   Sonstigethe residue obtained
3. 3
   Temperaturunder ice-cooling
4. 4
   workup.STIRRINGAfter stirring the mixture under ice-
5. 5
   Temperaturcooling for 0.5 hour
6. 6
   workup.WAITat room temperature for 1.5 hours
7. 7
   Extraktionextracted with methylene chloride
8. 8
   WaschenThe organic layer was washed with saturated aqueous sodium bicarbonate, and saturated brine successively
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Vorschrift

(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (996 mg) was dissolved in 4N hydrochloric acid/1,4-dioxane (12 ml), and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was concentrated to dryness, and the residue obtained was dissolved in methylene chloride (10 ml). After triethylamine (0.68 ml) was added thereto under ice-cooling, phenoxyacetyl chloride (0.34 ml) was dropwise added. After stirring the mixture under ice-cooling for 0.5 hour, and then at room temperature for 1.5 hours, the reaction mixture was poured into ice-water, and extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 1.05 g of the title compound.

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