Potassium Carbonate → HCID 69547056, compound

HRID 2184335Notes

Reaction equation

HRID 2184335 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@@H:12]1/[CH:17]=[CH:18]/[C:19]([C:21]1[O:22][C:23](Br)=[CH:24][CH:25]=1)=[O:20])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O.[BH4-].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)=O>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@@H:12]1[CH2:17][CH2:18][CH:19]([OH:20])[C:21]1[O:22][C:23]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH3:34])=[CH:24][CH:25]=1)[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 4311764Sodium borohydrideHCID 59075089HCID 59075089, compound

Product 1

HCID 69547056HCID 69547056, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

7-{(R)-2-[(E)-3-(5-Bromo-furan-2-yl)-3-oxo-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester was dissolved in anhydrous 1,4-dioxane (3 mL) under an argon atmosphere treated with potassium carbonate (130 mg, 0.94 mmol), 2-methylphenyl boronic acid (64 mg, 0.47 mmol), and bis(triphenylphosphine)palladiumdichloride (33 mg, 0.047 mmol). The yellow suspension was warmed to 55° C. for 15 hours and then the volatiles were removed. The mixture was then dissolved in methanol (10 mL) and stirred with sodium borohydride (ca. 35 mg, 0.9 mmol) for 20 minutes at ambient temperature and treated with acetone (1 mL). After removal of the volatiles, the residue was treated with methanol and the volatiles were removed once again. The residue was loaded onto 1 mm thick silica plates and the plates were developed two-times with 3% iso-propanol in dichloromethane. 7-{(S)-2-[3-hydroxy-3-(5-o-tolyl-furan-2-yl)-propyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester (54 mg) was obtained as an oil.

Workup

  1. customthe volatiles were removed
  2. dissolutionThe mixture was then dissolved in methanol (10 mL)
  3. customAfter removal of the volatiles
  4. additionthe residue was treated with methanol
  5. customthe volatiles were removed once again

Sources & evidence

ORD record
ord-4e709f2c274b45798190885fe5c8bac8
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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