2,6-Lutidine → HCID 86755965, compound

HRID 2184722Notes

Reaction equation

HRID 2184722 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-3fa9e5ce704c44a1a8b201f346e5b956
Source dataset
uspto-grants-2002_06
Patent number
US06399597B1

Reaction notes

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