Sodium hydride → HCID 58110330, compound

HRID 1914575Notes

Reaction equation

HRID 1914575 reaction equation
[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][CH2:3][CH2:2]1.[H-].[Na+].[F:13][C:14]([F:25])([F:24])[CH2:15]OS(C(F)(F)F)(=O)=O>CN(C=O)C.CO>[F:13][C:14]([F:25])([F:24])[CH2:15][N:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 15650612HCID 15650612, compound

Product 1

HCID 58110330HCID 58110330, compoundYield 144.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

cis-Decahydro-quinoxaline (0.104 g, 0.74 mmol) was dissolved in DMF (1 mL) and sodium hydride (60% in mineral oil, 0.015 g, 0.37 mmol) was added. After 5 minutes, trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (0.137 g, 0.37 mmol) was dissolved in a small amount of DMF and added to the mixture. Stirring was continued for 1 hour at room temperature then the material was diluted slightly with methanol and applied to a 10 g SCX-2 cartridge. This was washed with methanol then eluted using 2 N ammonia in methanol to afford 1-(2,2,2-trifluoro-ethyl)-decahydro-quinoxaline as a pale yellow oil (0.119 g).

Workup

  1. additionadded to the mixture
  2. waitwas continued for 1 hour at room temperature
  3. washThis was washed with methanol
  4. washthen eluted

Sources & evidence

ORD record
ord-b2e3dfd35dcd45f7a9e418234baaa2da
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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