Sodium hydride → HCID 89463121, compound

Participants

Reaction Steps

An ice cold solution of methyl 1-(4-fluorobenzyl)-2-((2-methoxy-2-oxoethyl)(methyl)carbamoyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-3-carboxylate (3.2 g, 7.65 mmol) in N,N-Dimethylformamide (DMF) (38.2 ml) was treated with NaH (0.398 g, 9.94 mmol). After 5 min, the reaction mixture was warmed to ambient temperature. After 45 min, the reaction mixture was poured into sat. aq. NH4Cl and extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford methyl 5-(4-fluorobenzyl)-9-hydroxy-7-methyl-6-oxo-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carboxylate (2.54 g, 6.57 mmol, 86% yield) as a yellow solid. LCMS (m/z) ES+=387 (M+1).

Provenance & Evidence