Methyl iodide → HCID 69038045, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.94 g (3.38 mmol) (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester dissolved in 20 ml of tetrahydrofurane at −78° C., 3.4 ml of lithium bis(trimethylsilyl)amide (1N solution in tetrahydrofurane) were added. The reaction mixture was stirred for 30 minutes at −78° C. and was allowed to reach room temperature. Iodomethane was slowly added and stirring was continued for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated NaHSO4 solution and separated. The aqueous phase was extracted twice with ethyl acetate (2×50 ml). The combined organic layers were washed with water (2×100 ml), with brine (1×100 ml), dried over MgSO4, filtered and evaporated. The residue was purified by chromatography (heptane/ethyl acetate=7:3) to yield 0.855 g (87%) of the product as a light yellow solid.

Provenance & Evidence