Sodium hydride → (4aS,8aS)-1-benzyldecahydroquinoxaline

HRID 1528290Notes

Reaction equation

HRID 1528290 reaction equation
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].FC(F)(F)S([O-])(=O)=O.Br[CH2:27][CH2:28][S+](C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].[NH4+]>C(Cl)Cl>[CH2:1]([N:8]1[C@@H:9]2[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[NH:15][CH2:28][CH2:27]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 25193077(2-Bromoethyl)diphenylsulfonium TrifluoromethanesulfonateHCID 70610516(1S,2S)-N-benzylcyclohexane-1,2-diamine

Product 1

HCID 66800513(4aS,8aS)-1-benzyldecahydroquinoxalineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The obtained (1S,2S)-N-benzylcyclohexane-1,2-diamine (2.90 g, 14.2 mmol) was dissolved in methylene chloride (284 nL). To the solution, 60% sodium hydride (1.99 g, 49.7 mmol) was added with ice-cooling and stirring in a nitrogen atmosphere. After 5 minutes, (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate (6.92 g, 15.6 mmol) was added to the reaction mixture with ice-cooling and stirring, and the mixture was stirred overnight at room temperature. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added dropwise in small portions, and the product was then extracted twice with methylene chloride (100 mL). The organic layers were combined and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane) to obtain (4aS,8aS)-1-benzyldecahydroquinoxaline (2.28 g, 70%) in a light brown solid form.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. stirringthe mixture was stirred overnight at room temperature
  5. extractionthe product was then extracted twice with methylene chloride (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was then distilled off under reduced pressure
  8. customThe obtained residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1557dab543bd4c438209fa2d138ac598
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

Loading…