Stannous chloride dihydrate → Benzyl 5-aminoisoindoline-2-carboxylate

Participants

Reaction Steps

To a solution of benzyl 5-nitro-1,3-dihydro-2H-isoindole-2-carboxylate (1.34 g, 4.49 mmol) in DMF (30 mL) was added SnCl2.2H2O (5.1 g, 22.5 mmol) as a powder. The mixture was stirred overnight. The reaction mixture was adjusted to basic pH with sat. aq. NaHCO3. The white precipitate formed was extracted with EtOAc (3×150 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide benzyl 5-amino-1,3-dihydro-2H-isoindole-2-carboxylate. LCMS calc.=269.1; found=268.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.46-7.34 (m, 5H); 7.12-6.93 (2 d, J=8.1, 1H); 6.66-6.53 (m, 2H); 5.25 (s, 2H); 4.69 (t, J=9.8 Hz, 4H); 3.71 (br s, 2H).

Provenance & Evidence