Methanol → HCID 59299449, compound

HRID 2235299Notes

Reaction equation

HRID 2235299 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH2:14][CH:15]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16]2=[O:26])=[C:9]([Cl:27])[CH:8]=1)(=O)=O.[C:30]([O-:33])(=[O:32])C.[Na+].[C]=O.[CH3:37]O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:37][O:33][C:30](=[O:32])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH2:14][CH:15]2[CH2:19][CH2:18][N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:16]2=[O:26])=[C:9]([Cl:27])[CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonateHCID 178418416HCID 178418416, compound

Product 1

HCID 59299449HCID 59299449, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Heat a mixture of 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (2.0 g, 4.2 mmol), anhydrous sodium acetate (1.04 g, 12.7 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (34 mg, 0.042 mmol) in methanol (60 mL) to 120° C. under 60 psi of carbon monoxide for 5 hours. Cool the reaction, extract with ethyl acetate and water and dry the organic layer (Na2SO4). The crude product is purified by normal phase chromatography (0 to 100% gradient of ethyl acetate in hexanes) to afford 1.21 g (75%) of the title compound: LC-MS (ES+) m/z=exact mass calcd for C19H23Cl2NO3 383, found 384 and 386 (M+1 and M+3, 100%).

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. extractionextract with ethyl acetate and water
  5. dry with materialdry the organic layer (Na2SO4)
  6. customThe crude product is purified by normal phase chromatography (0 to 100% gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-70a5f243fed74503804d552169e0bf82
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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