p-Toluenesulfonic acid → HCID 25196658, compound

HRID 1927578Notes

Reaction equation

HRID 1927578 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C@H:7]([NH:10][C@H](C2C=CC=CC=2)CO)[CH2:8][CH3:9])=[CH:4][CH:3]=1.CN.[O-][O-].[Na+].[Na+].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>CCO.O.C1COCC1.CC(OC)(C)C>[C:26]1([CH3:36])[CH:27]=[CH:28][C:29]([S:32]([OH:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1.[CH3:1][C:2]1[O:6][C:5]([C@H:7]([NH2:10])[CH2:8][CH3:9])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6329MethylamineHCID 14803Sodium peroxideHCID 11402700HCID 11402700, compound

Product 1

HCID 25196658HCID 25196658, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

80 g of (R)-2-[(R)-1-(5-Methyl-furan-2-yl)-propylamino]-2-phenyl-ethanol are dissolved in 160 ml of EtOH and the reaction mixture obtained is cooled to 5°. 40% methylamine in 23.5 ml of H2O are added and 70 g of sodium peroxide dissolved in 400 ml of H2O are added dropwise over a period of 1.5 hours at 5°. The reaction mixture obtained is stirred for 1.5 hours at rt, filtered and the filtrate obtained is washed with TBME, H2O and brine and the organic portion is dried over Na2SO4, filtered and solvent is evaporated. A residue obtained is dissolved in 80 ml of THF and is added dropwise to a solution of para-toluenesulfonic acid in 150 ml of THF at 0°. The reaction mixture obtained is stirred for 1 hour at rt, 200 ml of TBME are added and stirring is continued overnight. A solid is obtained and collected by filtration, washed with TBME and dried. The title compound is obtained.

Workup

  1. customthe reaction mixture obtained
  2. temperatureis cooled to 5°
  3. additionare added dropwise over a period of 1.5 hours at 5°
  4. customThe reaction mixture obtained
  5. filtrationfiltered
  6. customthe filtrate obtained
  7. washis washed with TBME, H2O and brine
  8. dry with materialthe organic portion is dried over Na2SO4
  9. filtrationfiltered
  10. customsolvent is evaporated
  11. customA residue obtained
  12. customThe reaction mixture obtained
  13. stirringis stirred for 1 hour at rt
  14. stirringstirring
  15. waitis continued overnight
  16. customA solid is obtained
  17. filtrationcollected by filtration
  18. washwashed with TBME
  19. customdried

Sources & evidence

ORD record
ord-3e788ed763a6427297fe6a8d26887122
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

Loading…