Sodium Bicarbonate → HCID 89462631, compound

Participants

Reaction Steps

An ice cold suspension of 5-(4-fluorobenzyl)-8-(hydroxymethyl)-7-methyl-9-(p-tolyl)-3,4,5,7-tetrahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridin-6(1H)-one (333 mg, 0.770 mmol) and NaHCO3 (323 mg, 3.85 mmol) in Dichloromethane (DCM) (7700 μl) was treated with DMP (653 mg, 1.540 mmol). Upon complete addition of the DMP the cooling bath was removed. After 2 h, the reaction mixture was quenched by the addition of sat. aq. Na2S2O3 and the mixture was stirred for 10 min. EtOAc was added and the layers partitioned. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by ISCO (0-50% EtOAc-hexanes) to afford 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde (150 mg, 0.348 mmol, 45.3% yield). LCMS (m/z) ES+=431 (M+1).

Provenance & Evidence