Potassium Iodide → HCID 90231437, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.0 g (10.83 mmol) ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (Intermediate 2) in 55 mL of anhydrous tetrahydrofuran at −78° C. was added slowly a solution of 1 M lithium bis(trimethylsilyl)amide in tetrahydrofuran (24 mL, 24 mmol). The solution was stirred at −78° C. for 30 min. A solution of 5.35 g (28.2 mmol) 1-chloromethyl-2-methyl-naphthalene in 15 mL of tetrahydrofuran was slowly added. The reaction mixture was stirred at −78° C. for 10 min, the cooling bath was removed and the mixture stirred overnight. Potassium iodide (1.8 g, 10.83 mmol) was added to the mixture. After 2 h, water and ethyl acetate were added to the mixture, the organic layer was washed with 10% aqueous sodium bisulfate, brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated. The residue was purified by silica gel chromatography to afford the title compound (3.2 g) as a light yellow solid. LC-MS: 432 (M+H).

Provenance & Evidence