Water → N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide

Participants

Reaction Steps

To a solution of 1.3 g of diethyl 4-[2-(2-nitro-benzenesulfonylamino)-ethoxy]-pyridine-2,6-dicarboxylate in 200 mL of ethanol was successively added 315 mg of sodium borohydride and 941 mg of CaCl2. The mixture was stirred for 1 hour 30 minutes at room temperature and 50 ml of water were then added thereto. The ethanol was removed under reduced pressure and 50 ml of water were added to the residue obtained; the aqueous phase was extracted 3× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. 1.06 g of N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide were obtained. LC/MS (A): tr=0.57 min; [M+H]+: m/z 384.

Provenance & Evidence