HCID 54275101, compound → HCID 54427490, compound

Participants

Reaction Steps

(±)-(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(4,5-dichloro-2-nitroanilino)-1,2-cyclopentanediyl diacetate (4.30 g, 9.28 mmol) in isopropanol (250 mL) was shaken with Raney nickel (Aldrich, slurry in water, 400 mg wet) under hydrogen (50 psi) on a Parr shaker for 2.75 hours. Catalyst was filtered off with Celite and the filtrate-wash (350 mL) stored at -5° C. Yellow crystals of title compound formed slowly (2.35 g, 58%), m.p. 124°-125° C.; 1H-NMR(DMSO-d6)δ: 6.70 and 6.57 (both s, 1 each, 2 aromatic CH), 5.15-4.9 (m, 5, NH2, NH, and 2 OCH), 4.2-4.0 (m, 2, CH2O), 3.9-3.75 (m, 1, NCH), 2.5-2.4 (m overlapping solvent, CH2), 2.07, 2.04, and 2.01 (all s, 9, 3 CH3), 1.4-1.2 (m, 1, CH); mass spectrum(CI): 433(M+1).

Provenance & Evidence