(+/-)-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
Reaction equation
COC1C=CC(C[N:8]2[CH2:12][CH2:11][C:10]3([CH2:21][CH2:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:22]([O:24][CH3:25])=[O:23])[CH:18]=4)[CH2:13]3)[C:9]2=[O:26])=CC=1>CC#N.O>[O:26]=[C:9]1[C:10]2([CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22]([O:24][CH3:25])=[O:23])[CH:18]=3)[CH2:13]2)[CH2:11][CH2:12][NH:8]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- waitat 50° C. for 4 h
- temperatureto cool
- customThe CH3CN was removed under reduced pressure
- customthe residual mixture was partitioned between dilute aqueous NaHCO3 (100 mL) and EtOAc (200 mL)
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was triturated with EtOAc
Sources & evidence
- ORD record
- ord-7b9c9ab8796b414981a4140b5b87d7cf
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390798B2
Reaction notes
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