Toluene → 4-[(1R,7S,7aR)-7-tert-Butyldimethylsilanoxy-1-methyl-3-oxohexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

Participants

Reaction Steps

To a solution of crude 80F (˜0.068 mmol) in CH2Cl2 (2 mL) was added i-Pr2NEt (36 μL, 0.20 mmol) followed by 20% phosgene in toluene (50 μL, 0.1 mmol)-dropwise. The reaction was stirred at rt for 4 days and no desired product was formed. The solvent was removed and the residue was dissolved in 1,2-dichloroethane (2 mL) and treated with i-Pr2NEt (108 μL) at 80° C. for 3 h. Reaction was concentrated and the residue was purified by preparative TLC (30% EtOAc/hexane) to provide the title compound 80G (11 mg): MS (ES) m/z 420.5 [M+H]+; HRMS calcd for C21H31N3O2C1Si 420.1874, found 420.1870.

Provenance & Evidence