Phosgene → HCID 118101199, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 20E (123 mg, 0.149 mmol) in acetonitrile (3 mL) and dichloromethane (6 mL) was cooled to 0° C. To this solution was added phosgene (20% in toluene, 0.081 mL, 0.164 mmol). The mixture was stirred at 0° C. for 5 min, and rt for 1 h. The mixture was bubbled with Ar for 10 min to remove excess phosgene. The resulting solution was added dropwise over 3 h via a syringe pump into a solution of TEA (0.208 mL, 1.489 mmol) in CH2Cl2 (260 mL) at rt. The solution was stirred at rt for 16 h. The solvent was concentrated and the crude product was purified by flash chromatography to give a mixture of diastereoisomers (60 mg, 47.3% yield). The diastereoisomers were separated by a prep chiral HPLC to give 20F (22 mg, 0.026 mmol, 37.9% yield).

Provenance & Evidence