Sulfuric acid magnesium salt (1:1) → methyl (3S)-3-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-1-carboxylate

HRID 64436

Reaktionsgleichung

Reaktionsgleichung von HRID 64436
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([O:13][CH3:14])=[O:12])[CH2:3]1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C@@H:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]([C:11]([O:13][CH3:14])=[O:12])[CH2:3]2)[CH3:24])=[CH:19][CH:18]=1

Komponenten

8

Edukt 5

HCID 24083Sulfuric acid magnesium salt (1:1)2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 793467(S)-1-(4-Methoxyphenyl)ethylamineHCID 2753058Methyl 3-oxo-2,3-dihydro-1H-indene-1-carboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 86713453methyl (3S)-3-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1 g of methyl 3-oxoindane-1-carboxylate in 10 ml of toluene were added 0.78 ml of (1S)-1-(4-methoxyphenyl)ethanamine and 100 mg of p-toluenesulfonic acid monohydrate, followed by heating to reflux for 5 hours using a Dean-Stark type reflux device. Then, 634 mg of magnesium sulfate was added thereto, followed by heating to reflux for 5 hours using a Dean-Stark type reflux device. Further, 634 mg of magnesium sulfate was added thereto, followed by heating to reflux for 5 hours using a Dean-Stark type reflux device. The insoluble material was removed by filtration and the solvent was then evaporated under reduced pressure to obtain an intermediate product. To a solution of the obtained intermediate product in 17 ml of ethanol was added 209 mg of sodium borohydride under ice-cooling, followed by stirring for 1 hour under ice-cooling. The solvent was evaporated under reduced pressure, and to the obtained residue were added water, a saturated aqueous sodium hydrogen carbonate solution, and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.195 g of methyl (3S)-3-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-1-carboxylate.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux for 5 hours
  3. temperaturereflux device
  4. temperatureby heating
  5. temperatureto reflux for 5 hours
  6. temperaturereflux device
  7. temperatureby heating
  8. temperatureto reflux for 5 hours
  9. temperaturereflux device
  10. customThe insoluble material was removed by filtration
  11. customthe solvent was then evaporated under reduced pressure
  12. customto obtain an intermediate product
  13. temperaturecooling
  14. temperaturecooling
  15. customThe solvent was evaporated under reduced pressure
  16. additionto the obtained residue were added water
  17. customa layer separation operation
  18. washThe organic layer was washed with water and saturated brine
  19. dry with materialdried over anhydrous magnesium sulfate
  20. customthe solvent was evaporated under reduced pressure
  21. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9349328707fc41c88b1215c50e613905
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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