Potassium Iodide → HCID 86755139, compound

HRID 377332Notes

Reaction equation

HRID 377332 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:22]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)[CH2:21][CH2:20][CH:19]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C1(C2N=C(C3[C@H](CC4C=CC=C(O)C=4)CCC=3)OC=2C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].BrC[C:74]([O:76][CH3:77])=[O:75].[I-].[K+]>C(Cl)Cl.C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:22]([CH2:23][C:24]4[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=4)[O:30][CH2:31][C:74]([O:76][CH3:77])=[O:75])[CH2:21][CH2:20][CH:19]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 60984Methyl bromoacetateHCID 10927656HCID 10927656, compoundHCID 56979827HCID 56979827, compound

Product 1

HCID 86755139HCID 86755139, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (+)-(5S)-1-(4,5-diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene (2.33 g) in methylene chloride (10 ml), was added boron tribromide in methylene chloride (1M, 9 ml) at 0C. After 3.5 hours stirring at the same temperature, the reaction mixture was washed with water and saturated aqueous sodium hydrogencarbonate. Drying (sodium sulfate) and removal of solvent afforded a yellow syrup containing (+)-(5S)-1-(4,5-diphenyloxazol-2-yl)-5-(3-hydroxybenzyl)cyclopentene. An acetonitrile solution (20 ml) of the yellow syrup, potassium carbonate (1.30 g), methyl bromoacetate (0.98 g) and potassium iodide (a catalytic amount) was stirred under reflux for 3.5 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with 1N hydrochloric acid, water and brine. Drying (sodium sulfate) and removal of solvent at reduced pressure followed by flash chromatography over 50 g of silica afforded (+)-methyl [3-[[(1S)-2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl]phenoxy]acetate (2.10 g, 98.2% ee) as a yellow oil.

Workup

  1. washthe reaction mixture was washed with water and saturated aqueous sodium hydrogencarbonate
  2. customDrying
  3. custom(sodium sulfate) and removal of solvent
  4. customafforded a yellow syrup
  5. temperatureunder reflux for 3.5 hours
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  8. washThe organic layer was washed with 1N hydrochloric acid, water and brine
  9. customDrying
  10. custom(sodium sulfate) and removal of solvent at reduced pressure

Sources & evidence

ORD record
ord-29b8581cd03546cb818fad73b86a437d
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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