2,7-Naphthyridine-2(1H)-carboxylic acid, 3,4-dihydro-, 1,1-dimethylethyl ester → tert-Butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl 3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (1.00 g, 4.27 mmol, 1 eq) and Pd(OH)2 (400 mg, 0.1 eq) in 150 mL of acetic acid was heated at 80° C. overnight under Hz, then cooled to room temperature, filtered and concentrated in vacuo. To this, 100 mL of water was added. The mixture was adjusted to pH 7-8 with NH3—H2O, extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (700 mg, 69%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 241.1 (M+1).

Provenance & Evidence