2,6-Lutidine → HCID 86755965, compound

HRID 369729Notes

Reaction equation

HRID 369729 reaction equation
[N:1]([CH2:4][C@@H:5]([CH3:8])[CH2:6]O)=[N+:2]=[N-:3].N1C(C)=CC=CC=1C.[O-:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19].[N:25]12[CH2:32][CH2:31][N:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2>C(Cl)Cl.CC#N>[O-:20][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:19])=[O:17].[N:1]([CH2:4][C@@H:5]([CH3:8])[CH2:6][N+:25]12[CH2:32][CH2:31][N:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 9237DabcoHCID 2758875TrifluoromethanesulfonateHCID 10582768HCID 10582768, compound

Product 1

HCID 86755965HCID 86755965, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

(R)-(-)-3-azido-2-methylpropanol (0.64 g, 5.56 mmol) was dissolved in CH2Cl2 (40 mL). 2,6-lutidine (1.9 mL, 16.3 mmol) was added at -20° C. followed by adding trifalic anhydride (1.4 mL, 8.32 mmol). The mixture was kept in -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 (1.33 g). The triflate (0.7 g, 2.83 mmol) was reacted with 1,4-diazabicyclo[2.2.2]octane (0.31 g, 2.77 mmol) in CH3CN for 3 hrs. The solvent was removed and the residue was dried under vacuum to give the product (1.0 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 (1.33 g)
  5. customThe solvent was removed
  6. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-e1e0fa30a01343a4a9c1edf374c9b8ee
Source dataset
uspto-grants-2000_10
Patent number
US06140318

Reaction notes

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