Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:15])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1)=[O:4].[BH4-].[Na+].[OH-].[Na+].Cl>CO>[F:15][C:8]1[CH:7]=[CH:6][C:5]([CH:3]2[CH2:2][O:4]2)=[CH:10][C:9]=1[S:11]([NH2:14])(=[O:13])=[O:12]
A solution of 0.5 g (1.7 mmol) of 5-bromoacetyl-2-fluoro-benzenesulfonamide V in 20 mL MeOH was cooled to 0° C. NaBH4 26 mg (0.67 mmol) was added and the reaction was stirred at 0° C. for 15 min. 4 mL of 1N NaOH was added and the reaction was stirred at 0° C. for 4 hrs. The reaction was adjusted to pH 6 by addition of dilute HCl. The volatiles were evaporated and the residue dissolved in EtOAc, washed with H2O, dried over Na2SO4 and evaporated. The product was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH::9/1 to give 180 mg of VI (48%); mp 100-103° C.TLC:CH2Cl2/MeOH::9/1 single-spot material Rƒ 0.65.1H-NMR (300 MHz DMSO-D6) δ: (2.82, m, 1H), (3.14, m, 1H), (4.06, m, 1H), (7.40, t, 1H), (7.56, m, 1H), (7.66, m, 3H).
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