[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[N:13]([CH2:19][CH:20]=[CH2:21])[CH2:12]1.[BH4-].[Na+].CO.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[N:13]([CH2:19][CH:20]=[CH2:21])[CH2:12]1
4-(2-Fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide (1.303 g, 4.15 mmol) and cuprous bromide: dimethyl sulfide complex (0.855 g, 4.15 mmol) are stirred at ice temperature in dry THF (30 ml). Sodium borohydride (1.25 g, 33.07 mmol) is added and the mixture stirred for 20 min. Methanol (10 ml) is carefully added over 30 min followed by ammonium chloride solution (50 ml). The mixture is extracted with methylene chloride (2×100 ml), washed with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated to yield the product as a cream solid (1.178 g, 100%) mp 96°.
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