Dichloromethane → HCID 10384329, compound

HRID 2181805Notes

Reaction equation

HRID 2181805 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9]C.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH3:28][CH:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]1[S:11]([C:5]1[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=1)(=[O:13])=[O:12]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482336HCID 22482336, compound

Product 1

HCID 10384329HCID 10384329, compoundYield 57%

Procedure

A stirred suspension of 5-[(3,4-dimethoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (988 mg, 2.5 mmol) and cyclohexene (4.11 g, 50 mmol) was treated at room temperature under nitrogen with a solution of 1.0 M boron tribromide in dichloromethane (15 mL, 15 mmol). After stirring for approximately two hours at room temperature, the reaction was quenched with methanol (20 mL) and diluted with dichloromethane. The mixture was washed sequentially with an aqueous potassium carbonate solution, a saturated, aqueous, sodium chloride solution, and water. The organic phase was dried over anhydrous sodium sulfate, filtered through a short column of silica gel, and eluted with ethyl acetate. The ethyl acetate phase was evaporated in vacuo to a crude residue (1.0 g). The crude residue was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g) with gradient elution of between 10% to 70% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min; and afforded, after evaporation of the solvent, a colorless solid. Crystallization of the colorless solid from a mixture of ethyl acetate-diethyl ether-hexane yielded the title compound (0.523 g, 1.42 mmol, 57%) as a colorless, amorphous solid, m.p. 163-165° C.;

Workup

  1. customthe reaction was quenched with methanol (20 mL)
  2. additiondiluted with dichloromethane
  3. washThe mixture was washed sequentially with an aqueous potassium carbonate solution
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered through a short column of silica gel
  6. washeluted with ethyl acetate
  7. customThe ethyl acetate phase was evaporated in vacuo to a crude residue (1.0 g)
  8. customThe crude residue was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g) with gradient elution of between 10% to 70% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min
  9. customand afforded
  10. customafter evaporation of the solvent
  11. customCrystallization of the colorless solid
  12. additionfrom a mixture of ethyl acetate-diethyl ether-hexane

Sources & evidence

ORD record
ord-bcd0b3cd154e48a1957bc35a4956542d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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