[C:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:17]([NH:24][OH:25])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CCC[N+](CCC)(CCC)CCC.[O-]I(=O)(=O)=O>C(Cl)Cl>[C:20]([O:19][C:17]([N:24]1[C@H:4]2[CH2:5][CH2:6][C@:1]([CH2:7][CH2:8][O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH:2]=[CH:3]2)[O:25]1)=[O:18])([CH3:23])([CH3:22])[CH3:21](2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene (9) (6 g, 28 mmol) is dissolved in 280 ml of dry methylene chloride and cooled down to 0° C. After addition of molecular sieves (6 g, UOP Type 4A) and N—BOC-hydroxylamine (5.6 g, 42 mmol) in small portions, tetrapropylammonium(meta)periodate (10.8 g, 28 mmol) is added slowly in small portions the mixture was stirred for 1 h. Then the mixture is diluted with CH2C12 and cooled to −10° C. 2M Na2S2O5 solution is added slowly (exothermic!). The mixture is washed with water, dried over Na2SO4 and evaporated under reduced pressure. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).
Wird geladen…