Hydrochloric Acid → (S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Triphosgene (0.58 g) dissolved in dichloromethane (10 mL) is added dropwise to a solution of adamantane-1,4-diol (1.00 g) and pyridine (10 mL) in dichloromethane (30 mL) cooled to −10° C. The solution is stirred at ca. 0° C. for 2.5 h and then (S)-3-hydroxy-pyrrolidine (0.50 mL) is added. The resulting solution is stirred overnight while warming to room temperature. The solution is then diluted with dichloromethane (50 mL) and chilled in an ice bath. 4 M hydrochloric acid (25 mL) is added and the resulting mixture is stirred for 5 min. The organic phase is separated and washed with 4 M hydrochloric acid and water. The organic phase is dried (MgSO4) and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 0.98 g (59% of theory); Mass spectrum (ESI+): m/z=282 [M+H]+.

Herkunft & Nachweise