Carbon Dioxide → HCID 70171841, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-1-(tert-butoxycarbonyl)-3-({2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}amino)pyrrolidine, as described above in Step E, (411 mg, 0.786 mmol) in CH2Cl2 (10 mL), was added triethylamine (0.110 mL, 0.786 mmol) and the mixture was cooled to −78° C. Solid CO2 (1.73 g, 39.3 mmol) was added and after 30 min, triisopropylsilyl chloride (0.172 mL, 0.802 mmol) was added and the reaction mixture was warmed to ambient temperature. After 1 hour, the reaction was diluted with water and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 3% MeOH—0.1% to 0.3% NH4OH, to yield the above-titled compound.

Provenance & Evidence