Benzyl Bromide → HCID 69052907, compound

Participants

Reaction Steps

To a suspension of hexane-washed sodium hydride (6 mg of 60% dispersion in mineral oil, 0.15 mmol) in 1 mL THF was added (±)-trans-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 74, Part A (25 mg, 0.076 mmol) in 2 mL of THF. The mixture was stirred at ambient temperature for 30 min, at which time gas evolution had ceased. Then there was added benzyl bromide (0.027 mL, 0.23 mmol) and the resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was quenched with 1N HCl and diluted with ethyl acetate. The organics were washed sequentially with sat'd aq. NaHCO3, and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 4:1 hexane/EtOAc) to afford 28 mg (88%) of the title compound as an oil. LRMS (ESI): 421.1 (M+H)+.

Provenance & Evidence