Dichloromethane → HCID 10473142, compound

HRID 2181787Notes

Reaction equation

HRID 2181787 reaction equation
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]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 69355279HCID 69355279, compound

Product 1

HCID 10473142HCID 10473142, compound

Procedure

The title compound was prepared from (R)-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.38 g, 1.04 mmol), cyclohexene (0.27 mL, 2.61 mmol), and 1.0 M boron tribromide in dichloromethane (6.27 mL, 6.27 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by flash column chromatography on silica gel, eluting with dichloromethane, to yield 4-{[(R)-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol* (0.26 g, 0.74 mmol, 71%) as a white, solid, single enantiomer, m.p. 181-183° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with dichloromethane

Sources & evidence

ORD record
ord-cfdc05d9d99c4fa29e60ccf210b3430b
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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