Sodium Hydroxide → HCID 69057496, compound

Participants

Reaction Steps

To a solution of (3aR,9bS)-tert-butyl 8-ethyl-6-methoxy-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Example 51, Part B (686 mg, 1.98 mmol) in 100 mL of methylene chloride was added boron tribromide (2.38 mL of a 1 M solution in methylene chloride, 2.38 mmol) dropwise at ambient temperature. The solution was allowed to stir for 8 h and then there was added 100 mL of 1 N sodium hydroxide followed by followed by di-tert-butyl dicarbonate (648 mg, 2.97 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction was diluted with 1 N HCl to give a pH of −5-6. The layers were separated and the organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified (ISCO, elution with 0-50% EtOAc/hexane) to afford 413 mg (63%) of the title compound as a white solid. LRMS (ESI): 333.2 (M+H)+.

Provenance & Evidence