1,4-Dioxane → HCID 68539560, compound

HRID 1441669Notes

Reaction equation

HRID 1441669 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.[CH3:47][C:48]([CH3:51])([O-:50])[CH3:49].[Na+].C(OC([N:60]1[CH2:65][CH2:64][CH:63]([C:66](=[O:84])[N:67]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=2Br)[CH2:68][CH2:69][O:70][CH:71]2[CH2:76][CH2:75][CH2:74][CH2:73][O:72]2)[CH2:62][CH2:61]1)=O)(C)(C)C.[O:85]1CCOC[CH2:86]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]>[O:72]1[CH2:73][CH2:74][CH2:75][CH2:76][CH:71]1[O:70][CH2:69][CH2:68][N:67]1[C:77]2[C:82](=[CH:81][C:80]([C:86]([O:50][C:48]([CH3:51])([CH3:49])[CH3:47])=[O:85])=[CH:79][CH:78]=2)[C:63]2([CH2:64][CH2:65][NH:60][CH2:61][CH2:62]2)[C:66]1=[O:84]

Participants

6

Reactant 4

HCID 312751,4-Dioxane2×HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 58878509HCID 58878509, compound

Product 1

HCID 68539560HCID 68539560, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Pd(dba)2 (0.068 g, 0.109 mmol), rac-BINAP (0.078 g, 0.085 ml) and sodium tert-butoxide (0.22 g, 2.28 mmol) were combined into a pressure flask. To the reaction mixture was then added dry 1,4-dioxane (3 mL) under nitrogen and the resulting mixture stirred for 1 minute. To the reaction mixture was then added, under nitrogen, a solution of 4-{(2-bromo-phenyl)-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester (0.78 g, 1.52 mmol) in dry 1,4-dioxane (9 mL). The pressure flask was sealed and degassed under high vacuum and left under nitrogen. The reaction mixture was stirred at 110° C. for 6 hours and then partitioned with aqueous 0.5 M citric acid, water and methylene chloride. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a solid. The solid was purified via flash chromatography (50% ethyl acetate/hexanes) to yield the title compound as a foam.

Workup

  1. additionTo the reaction mixture was then added, under nitrogen
  2. customThe pressure flask was sealed
  3. customdegassed under high vacuum
  4. waitleft under nitrogen
  5. stirringThe reaction mixture was stirred at 110° C. for 6 hours
  6. custompartitioned with aqueous 0.5 M citric acid, water and methylene chloride
  7. washThe organic layer was washed with brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. customthe solvent evaporated in vacuo
  11. customto yield a solid
  12. customThe solid was purified via flash chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-00956a7ce8954e6ea52a57c8588c3e2c
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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