Cesium carbonate → HCID 59299494, compound

HRID 2235286Notes

Reaction equation

HRID 2235286 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[C:59]1[CH:64]=[C:63]([Cl:65])[C:62]([CH2:66][CH:67]2[CH2:71][CH2:70][N:69]([CH:72]3[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]3)[C:68]2=[O:78])=[C:61]([Cl:79])[CH:60]=1)(=O)=O.C(=[NH:95])(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[NH2:95][C:59]1[CH:64]=[C:63]([Cl:65])[C:62]([CH2:66][CH:67]2[CH2:71][CH2:70][N:69]([CH:72]3[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]3)[C:68]2=[O:78])=[C:61]([Cl:79])[CH:60]=1

Participants

10

Reactant 6

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 634876Binap, (A+-)-HCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate

Product 1

HCID 59299494HCID 59299494, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Place Pd2(dba)3 (710 mg, 3.16 mmol), BINAP (2.95 g, 4.74 mmol), and Cs2CO3 (15.0 g, 47.0 mmol) in a dry flask. Add 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (15.0 g, 32.0 mmol), benzophenone imine (8.60 g, 47.4 mmol), and 750 mL of toluene. Heat at 100° C. overnight. Cool to room temp and filter. Remove toluene under reduced pressure. Dissolve crude imine in MeOH and add sodium acetate (5.20 g, 63.0 mmol) and hydroxylamine hydrochloride (4.40 g, 63.0 mmol). Stir at room temp for 45 min. Pour into water and extract with CH2Cl2. Dry, filter, and concentrate. Purify the residue by Biotage eluting with a mixture of EtOAc and hexanes (30:70 to 50:50) to give the title compound (7.0 g, 65%): Mass spectrum (apci) m/z=341.2 (M+H).

Workup

  1. temperatureCool to room temp
  2. filtrationfilter
  3. dissolutionDissolve crude imine in MeOH
  4. extractionextract with CH2Cl2
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by Biotage
  9. washeluting with a mixture of EtOAc and hexanes (30:70 to 50:50)

Sources & evidence

ORD record
ord-96004242a9124c46b123af5b301d413f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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