(+/-)-Methyl 1'-(4-methoxybenzyl)-2'-oxo-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-6-carboxylate → (+/-)-Methyl 2'-oxo-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-6-carboxylate

Participants

Reaction Steps

To a stirred solution of (±)-methyl 1′-(4-methoxybenzyl)-2′-oxo-3,4-dihydro-1H-spiro[naphthalene-2,3′-pyrrolidine]-6-carboxylate from Step E (270 mg, 0.712 mmol) in CH3CN (9 mL) was added dropwise a solution of ceric ammonium nitrate (1.95 g, 3.56 mmol) in H2O (9 mL). The resulting mixture was stirred at ambient temperature for 18 h, then at 50° C. for 4 h, then allowed to cool. The CH3CN was removed under reduced pressure, and the residual mixture was partitioned between dilute aqueous NaHCO3 (100 mL) and EtOAc (200 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with EtOAc to give the title compound. MS: m/z=260 (M+1).

Provenance & Evidence