1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9886858, compound

HRID 613448Notes

Reaction equation

HRID 613448 reaction equation
C(O[C@H:5]1[C@H:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:21][CH2:22][CH2:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:12]=2)[O:7][C:6]1([CH3:30])[CH3:29])(=O)C.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CC(=O)OCC>[F:28][C:25]([F:26])([F:27])[CH2:24][CH2:23][CH2:22][O:21][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[O:7][C:6]([CH3:30])([CH3:29])[CH:5]=[C:14]2[N:15]([CH3:20])[S:16]([CH3:19])(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86754985HCID 86754985, compound

Product 1

HCID 9886858HCID 9886858, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.5 g of (±)-trans-N-[3-acetoxy-6-(4,4,4-trifluorobutoxy)-2,2-dimethylchroman-4-yl]-N-methyl-methanesulfonamide (example 21) and 6.8 g of DBU in 30 ml of toluene was heated at 105° C. for 20 h. The reaction mixture was diluted with EA and washed with hydrochloric acid until the aqueous phase gave an acidic reaction. The mixture was washed with sodium bicarbonate solution, dried over magnesium sulfate, concentrated i. vac. and triturated with heptane, giving 1.7 g N-[6-(4,4,4-trifluorobutoxy)-2,2-dimethyl-2H-chromen-4-yl]-N-methyl-methanesulfonamide; m.p. 118° C.

Workup

  1. washwashed with hydrochloric acid until the aqueous phase
  2. customgave
  3. customan acidic reaction
  4. washThe mixture was washed with sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated i
  7. customand triturated with heptane

Sources & evidence

ORD record
ord-994a84f893834e97b45ae9a0711edc0e
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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