Sodium hydride → HCID 91189016, compound

Participants

Reaction Steps

To a suspension of sodium hydride (33 mg of 60% dispersion in mineral oil, hexane-washed, 0.87 mmol) in 4 mL of 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 (191 mg, 0.58 mmol) in 10 mL of THF. The resulting mixture was stirred at ambient temperature for 30 min, at which time gas evolution has ceased. Then there was added methyl bromoacetate (0.082 mL, 0.87 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction was quenched with 10 mL of 1 N HCl and extracted with ethyl acetate. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 15-25% EtOAc/hexane) to afford 180 mg (77%) of the title compound. LRMS (ESI): 403.1 (M+H)+.

Provenance & Evidence