Methyl iodide → HCID 69054271, compound

Participants

Reaction Steps

To a suspension of NaH (8.5 mg of 60% in mineral oil, hexane-washed, 0.21 mmol) in 2 mL of THF at ambient temperature was added (3aR,9bS)-tert-butyl 5-oxo-6-(trifluoromethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 13, Part A (50 mg, 0.14 mmol) as a solution in 2 mL of THF. The reaction was stirred for 20 min, at which time gas evolution had ceased and the reaction mixture was homogeneous. Then there was added iodomethane (0.022 mL, 0.35 mmol) and the reaction was allowed to stir at ambient temperature for 18 h. The reaction was quenched with water, diluted with EtOAc and washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 3:1 hexane/EtOAc) to afford 40 mg (77%) of the title compound. LRMS (ESI): 371.12 (M+H)+.

Provenance & Evidence