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

Temperatur

-10 °C

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]+.

1. stirringThe resulting solution is stirred overnight
2. temperaturewhile warming to room temperature
3. temperaturechilled in an ice bath
4. stirringthe resulting mixture is stirred for 5 min
5. customThe organic phase is separated
6. washwashed with 4 M hydrochloric acid and water
7. dry with materialThe organic phase is dried (MgSO4)
8. concentrationconcentrated

ORD-Eintrag

ord-aa4f94b162ee4f46bfbaeb81dc283bc1

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09163012B2