2,6-Lutidine → HCID 22457555, compound

HRID 369728Notes

Reaction equation

HRID 369728 reaction equation
O[CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH2:3]1.N1C(C)=CC=CC=1C.[S:21]([O:28]S(C(F)(F)F)(=O)=O)([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].[O-]S(C(F)(F)F)(=O)=O.[N:44]12[CH2:51][CH2:50][N:47]([CH2:48][CH2:49]1)[CH2:46][CH2:45]2>C(Cl)Cl.CC#N>[O-:28][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][CH:2]([N+:44]23[CH2:51][CH2:50][N:47]([CH2:48][CH2:49]2)[CH2:46][CH2:45]3)[CH2:3]1)=[O:8])[CH:11]=[CH2:12]

Participants

8

Reactant 5

HCID 79372,6-LutidineHCID 9237DabcoHCID 67749Trifluoromethanesulfonic anhydrideHCID 2758875TrifluoromethanesulfonateHCID 15117216HCID 15117216, compound

Product 1

HCID 22457555HCID 22457555, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Hydroxy-1-allyloxycarbonylpyrrolidine (0.34 g, 1.99 mmol) was dissolved in CH2Cl2 (40 mL). 2,6-Lutidine (0.7 mL, 6 mmol) was added at -20° C. followed by adding triflic anhydride (0.5 mL, 2.97 mmol). The mixture was kept at -20° C. for 40 min, diluted with CH2Cl2, washed with water, 0.1 N HCl aqueous solution, water and brine, dried over Na2SO4 and concentrated to give the trifalte (0.63 g). The triflate (0.43 g, 1.42 mmol) was reacted with 1,4-diazabicyclo[2.2.2]octane (0.15 g, 1.34 mmol) in CH3CN overnight. The solvent was removed and the residue was dried under vacuum to give the product (0.42 g).

Workup

  1. washwashed with water, 0.1 N HCl aqueous solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the trifalte (0.63 g)
  5. customThe solvent was removed
  6. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-1950e263f15b429da687c2b11db59c67
Source dataset
uspto-grants-2000_10
Patent number
US06140318

Reaction notes

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