Methyl iodide → benzyl 1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate

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Reaction Conditions

Reaction Steps

To a solution of benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate (13) (Sherril R. G.; Sugg, E. E. Improved Synthesis and Resolution of 3-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones. J. Org. Chem. 1995, 60, 730-734) (1.00 g, 2.60 mmol) in anhydrous DMF (10 mL), kept at 0° C. under N2, NaH (60% dispersion in mineral oil, 0.10 g, 1 eq) was added in small portions. After 1.5 hr stirring at 0° C., methyl iodide (0.17 mL, 1.05 eq) was added at once; the mixture was stirred for additional 1.5 h at the same temperature, and then poured into a stirred solution of H2O (60 mL) containing aqueous sodium hydrogen sulphate (2 mL, 1 N). A solid precipitated, which was filtered, dried under vacuum, and then purified by flash chromatography (CH2Cl2/MeOH/NH3 99:1:0.1 as eluent) giving benzyl 1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate in 91% yield. M.p. 78-80° C.

Provenance & Evidence