Methylamine → HCID 118098696, compound

Participants

Reaction Steps

To a solution of 2-chloro-5-nitrobenzaldehyde (5 g, 26.9 mmol) in MeOH (100 mL), was added methylamine (33% in EtOH) (14.82 mL, 29.6 mmol). The mixture was stirred at rt for 1 h, cooled to 0° C. and treated with NaBH4 (1.223 g, 32.3 mmol). The mixture was stirred at rt for 30 min, then was concentrated. The residue was dissolved in THF (50 mL), treated with water (20 mL) and sat. NaHCO3 (20 mL). After stirring for 10 min, Cbz-Cl (4.62 mL, 32.3 mmol) was added dropwise. The mixture was stirred at rt over night. THF was removed under reduced pressure. The mixture was extracted with EtOAc (2×). The organic phase was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 120 g column and eluted with a gradient from 0 to 50% ethyl acetate/hexanes) to give 6A (7.39 g, 22.08 mmol, 82% yield) as a white solid. MS (ESI) m/z: 335.1 [M+1]+; 1H NMR (400 MHz, chloroform-d) δ ppm 7.97-8.13 (m, 2H) 7.55 (d, J=7.53 Hz, 1H) 7.27-7.45 (m, 5H) 5.11-5.26 (m, 2H) 4.58-4.72 (m, 2H) 3.03 (br. s., 3H), 3:2 rotamers.

Provenance & Evidence