Thiophenol → HCID 69053351, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans-tert-butyl 8-methoxy-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 72, Part C (0.43 g, 1.29 mmol) in 8 mL of N-methylpyrrolidinone was added thiophenol (0.15 mL, 1.42 mmol) and potassium carbonate (27 mg, 0.19 mmol). The resulting mixture was stirred in a sealed vial at 160° C. for 4 h. The solution was allowed to cool and was partitioned between ether and 1N NaOH. The aqueous layer was washed with ether. The combined organic layers were discarded. The aqueous layer was acidified with 12 N HCl, whereby a solid precipitated out of solution. The mixture was filtered and the solid washed with water and dried in vacuo to afford 0.26 g (65%) of the title compound as an off-white solid. LRMS (ESI): 319.3 (M+H)+.

Provenance & Evidence