tert-Butyl bromoacetate → HCID 59463562, compound

Participants

Reaction Steps

A mixture of ethyl 1,7-naphthyridine-3-carboxylate (905 mg, 4.476 mmol) and tert-butyl bromoacetate (1.0 g, 5.15 mmol) in CH3CN (15 mL) is refluxed overnight. Solvent is removed in vacuo and the residue is dissolve in MeOH (20 mL). To the solution is added NaBH4 (677 mg, 17.9 mmol) and the mixture is refluxed for 4 hr. The solvent is removed in vacuo and the residue is partitioned between water (30 mL) and EtOAc (30 mL). The layers are separated and the aqueous layer is extracted with EtOAc (20 ml). The combined extracts are washed with brine (20 mL), dried and evaporated. The residue is purified by flash column to give the title compound as a light yellow oil. MS (M+1): 321.2.

Provenance & Evidence