Pyrrolidine → HCID 67119030, compound

HRID 2076608Notes

Reaction equation

HRID 2076608 reaction equation
N1CCCC1.C([O:9][C:10]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[C:19]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][C:42]([O:44]CC=C)=[O:43])=[CH:37][CH:36]=3)=[C:31]([Cl:48])[CH:30]=2)[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C=C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]([O:14][C:12]([C:11]1[C:10]([OH:9])=[C:22]([C:23]([F:26])([F:24])[F:25])[CH:21]=[CH:20][C:19]=1[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[CH:37][C:38]([CH2:41][C:42]([OH:44])=[O:43])=[CH:39][CH:40]=2)=[C:31]([Cl:48])[CH:30]=1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 2

HCID 31268PyrrolidineHCID 67119334HCID 67119334, compound

Product 1

HCID 67119030HCID 67119030, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Pyrrolidine (0.525 ml, 6.29 mmol) and tetrakis(triphenylphosphine)palladium (0) (41 mg, 0.035 mmol) were added to a solution of tert-butyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-2-chloro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (960 mg, 1.56 mmol) obtained in Example (13-4) in a mixture of 1,4-dioxane (9.5 ml) and water (0.5 ml), and the mixture was stirred at room temperature for 3 hours. After water was poured into the reaction mixture and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=75/25-40/60) to give the title compound as a white powder (446 mg, yield: 74%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (three times)
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=75/25-40/60)

Sources & evidence

ORD record
ord-c0e287d6e52647d7b7e8384ade3459ab
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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