Methylamine → HCID 118092892, compound

Participants

Reaction Steps

To a flask with 2-fluoro-5-nitrobenzaldehyde (2 g, 11.83 mmol) in MeOH (60 mL) was added methylamine (33% in EtOH, 2.94 mL, 23.65 mmol). The reaction mixture was stirred at rt for 2 h, cooled to 0° C. Sodium borohydride (0.895 g, 23.65 mmol) was added and the mixture was stirred at rt for 1 h. Solvent was removed and the residue was suspended in THF (60.0 mL) and water (30.0 mL). The mixture was treated with sodium bicarbonate (2.98 g, 35.5 mmol), cooled to 0° C., and then CBZ-Cl (2.195 mL, 15.37 mmol) was added dropwise. The mixture was stirred rt overnight. The solvent was removed and the residue was dissolved in EtOAc. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to give 13A (3.6 g, 11.31 mmol, 96% yield) as a yellow oil. MS (ESI) (m/z): 341 (M+Na)+. 1H NMR (400 MHz, chloroform-d) δ ppm 8.04-8.28 (m, 2H) 7.28-7.50 (m, 5H) 7.21 (t, J=8.34 Hz, 1H) 5.19 (d, J=8.84 Hz, 2H) 4.51-4.68 (m, 2H) 3.01 (br. s., 3H).

Provenance & Evidence