Acetic Acid → HCID 86636261, compound

Participants

Reaction Conditions

Reaction Steps

Into the reaction was added tert-butyl (2-iodo-4-nitrobenzyl)methylcarbamate (4.90 g, 12.5 mmol), methanol (85 mL), acetic acid (14.2 mL) and iron (4.19 g, 75.0 mmol) powder. The reaction solution was heated at 50° C. for 1.5 h. After cooling to room temperature, the reaction solution was diluted with ethyl acetate and a saturated sodium carbonate solution. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The aqueous layer was extracted with ethyl acetate once. The combined organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to yield the desired product (4.10 g, 91%). LCMS calculated for C13H191N2O2Na (M+H)+: m/z=385.1.

Provenance & Evidence