Potassium Phosphate, Tribasic → 1-(3-Chloro-4-cyano-2-methylphenyl)-2-oxo-octahydrocyclopenta[b]-pyrrol-4-yl benzoate

HRID 642747Notes

Reaction equation

HRID 642747 reaction equation
[C:1]([O:9][CH:10]1[CH:17]2[CH:13]([C:14](=[O:18])[NH:15][CH2:16]2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:27][CH:28]1[CH:35]2[CH:31]([NH:32][C:33](=[O:36])[CH2:34]2)[CH2:30][CH2:29]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Cl:45][C:46]1[C:53]([CH3:54])=[C:52](I)[CH:51]=[CH:50][C:47]=1[C:48]#[N:49]>O1CCOCC1.[Cu]I>[C:1]([O:9][CH:10]1[CH:17]2[CH:13]([C:14](=[O:18])[N:15]([C:52]3[CH:51]=[CH:50][C:47]([C:48]#[N:49])=[C:46]([Cl:45])[C:53]=3[CH3:54])[CH2:16]2)[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:27][CH:28]1[CH:35]2[CH:31]([N:32]([C:52]3[CH:51]=[CH:50][C:47]([C:48]#[N:49])=[C:46]([Cl:45])[C:53]=3[CH3:54])[C:33](=[O:36])[CH2:34]2)[CH2:30][CH2:29]1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

Product 2

HCID 592595661-(3-Chloro-4-cyano-2-methylphenyl)-2-oxo-octahydrocyclopenta[b]-pyrrol-4-yl benzoateHCID 592595732-(3-Chloro-4-cyano-2-methylphenyl)-1-oxo-octahydrocyclopenta[c]-pyrrol-4-yl benzoate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a vial containing mixtures of compound 1I and 1J (100 mg, 0.4 mmol) obtained from previous step in dioxane (1 mL) were added CuI (15.6 mg, 0.08 mmol), K3PO4 (174 mg, 0.82 mmol), 1,2-cyclohexyldiamine (4.7 mg, 0.08 mmol) and compound 1E (136 mg, 0.49 mmol). The vial was sealed, and heated at 110° C. for 14 hr, cooled to RT. The solid was filtered off, and filtrate was concentrated. Purification by silica gel chromatography (5% to 100% EtOAc in hexanes, then 10% methanol in EtOAc) provide the mixtures of title compounds 1K and 1L (total 98 mg) as a yellow oil. MS (ES) m/z 395 [M+H]+.

Workup

  1. customThe vial was sealed
  2. temperaturecooled to RT
  3. filtrationThe solid was filtered off
  4. concentrationfiltrate was concentrated
  5. customPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-722b3a5356f24a2ab6d966e77bcf9ecd
Source dataset
uspto-grants-2010_04
Patent number
US07696241B2

Reaction notes

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