Dichloromethane → HCID 10341663, compound

HRID 2181791Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C@@H:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[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>>[C:26]1([C@H:25]2[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]=3[N:12]2[S:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)(=[O:11])=[O:10])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 69354088HCID 69354088, compound

Product 1

HCID 10341663HCID 10341663, compound

Procedure

The title compound was prepared from (S)-5-[(4-methoxyphenyl)sulfonyl]-6-phenyl-5,6-dihydrophenanthridine* (1.35 g, 3.16 mmol), cyclohexene (6.16 g, 75 mmol), and 1.0 M boron tribromide in dichloromethane (20 mL, 20 mmol) according to the procedure and in the same manner as described in Example 1, step b; and yielded, after chromatographic purification and crystallization from diethyl ether-hexane, 4-{[(S)-6-phenylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.627 g, 1.52 mmol, 48%) as a homogeneous, colorless, crystalline, single enantiomer*, m.p. 210-212° C.;

Workup

customand yielded
customafter chromatographic purification and crystallization from diethyl ether-hexane, 4-{[(S)-6-phenylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.627 g, 1.52 mmol, 48%) as a homogeneous, colorless, crystalline, single enantiomer*, m.p. 210-212° C.

Sources & evidence

ORD record: ord-80b82d0333d14cf18306005ced46e999
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894061B2

Reaction notes

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