Cyclohexene → 4-{[(S)-8-fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol

HRID 2224623Notes

Reaction equation

HRID 2224623 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:5]2[CH3:27].C1CCCCC=1.B(Br)(Br)Br>C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)(=[O:18])=[O:17])[C@H:5]2[CH3:27]

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 58597403(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 104742374-{[(S)-8-fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenolYield 90.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine (1.26 g, 3.29 mmol) was suspended in cyclohexene (6.0 mL, 59 mmol). Boron tribromide (20 mL, 1.0 M solution in dichloromethane) was added dropwise at room temperature. The solution was stirred for 20 hours. A solution of saturated, aqueous sodium bicarbonate (300 mL) was added dropwise and then the mixture was extracted with dichloromethane (6×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography (1:19 to 1:4 ethyl acetate:hexane) and then recrystallization (dichloromethane-hexane) to afford the title compound as white crystals (1.1 g, 90%), m.p. 193° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane (6×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel flash chromatography (1:19 to 1:4 ethyl acetate:hexane)
  6. customrecrystallization (dichloromethane-hexane)

Sources & evidence

ORD record
ord-19c5a2fec0194530bcc2436bd94fc26d
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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