Methyl iodide → HCID 9909686, compound

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Reaction Steps

To a solution of Example 7 (0.200 g, 0.50 mmol) in 5 mL of THF are added NaH (0.068 g, 1.56 mmol) and methyl iodide (125 μL, 2.0 mmol). After 2 hr of stirring at rt the reaction is judged to be complete by tlc monitoring (SiO2, DCM:MeOH (100:3)) and is quenched with a saturated aqueous solution of Na2CO3 (5 mL). Extraction with DCM, drying over MgSO4, concentration in vacuo, flash chromatography on a 2.5×12 cm2 column of silica gel using DCM:MeOH (95:5) as eluting solvent and removal of the solvent in vacuo gives the title compound as an oil. Slow addition of HCl (4 eq, 1M in Et2O) into a solution of the above compound in EtOH (2 mL) gives the hydrochloride salt of the title compound (0.39 g) as white crystals in a 60% yield. M.p.: 272° C.

Provenance & Evidence