Dichloromethane → 4-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol

反応式

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C@@H:25]([CH3:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH3:26][C@H:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]1[S:9]([C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1)(=[O:11])=[O:10]

参加物

反応物 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 58597406(S)-5-(4-Methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

生成物 1

HCID 104505944-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol

実験手順

The title compound was prepared from (S)-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.32 g, 1.02 mmol), cyclohexene (0.26 mL, 2.54 mmol), and 1.0 M boron tribromide in dichloromethane (6.1 mL, 6.1 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by column chromatography on silica gel, eluting with dichloromethane, to yield 4-{[(S)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.25 g, 0.72 mmol, 71%) as a white, solid, single enantiomer, m.p. 176-178° C.;