HCID 90928462, compound → HCID 69054321, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans tert-butyl 6-methyl-5-oxo-8-(trifluoromethylsulfonyloxy)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 91, Part A (265 mg, 0.59 mmol) was added diisopropylzinc (1.76 mL of a 1.0 M solution in toluene, 1.76 mmol). The reaction mixture was degassed with a stream of argon and then there was added bis(diphenylphosphino)ferrocene]-dichloropalladium (II) (22 mg, 0.029 mmol). The reaction mixture was allowed to stir at 65° C. for 18 h. The reaction was allowed to cool to ambient temperature and was quenched with 1N HCl. The mixture was diluted with ethyl acetate and the organics were washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.22 g of the title compound as an off-white solid, which was sufficiently pure to be employed directly in Part B. LRMS (ESI): 345.2 (M+H)+.

Provenance & Evidence