Sodium Sulfate → (2R*,3R*,4R*,6S*)-3-(2,5-Dimethoxybenzyl)amino-2-diphenylmethyl-6-hydroxymethyl-1-azabicyclo[2.2.2]octane

HRID 862125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862125
[H-].[Al+3].[Li+].[H-].[H-].[H-].CN(C)[C:9]([C@H:11]1[CH2:16][C@@H:15]2[CH2:17][CH2:18][N:12]1[C@@H:13]([CH:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:14]2[NH:19][CH2:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[O:29][CH3:30])=[O:10].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:30][O:29][C:22]1[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=1[CH2:20][NH:19][C@@H:14]1[C@@H:15]2[CH2:17][CH2:18][N:12]([C@H:11]([CH2:9][OH:10])[CH2:16]2)[C@@H:13]1[CH:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 70114647(2R*,4S*,5S*,6S*)-N,N-dimethyl-5-(2,5-dimethoxybenzyl)amino-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-2-carboxamide

Produkt 1

HCID 54206645(2R*,3R*,4R*,6S*)-3-(2,5-Dimethoxybenzyl)amino-2-diphenylmethyl-6-hydroxymethyl-1-azabicyclo[2.2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Into a suspension of lithium aluminum hydride (LiAlH4) (92 mg, 2.4 mmole) in dry THF (10 ml) at 0° C. was added a solution of compound 35 (417 mg, 0.8 mmole) in dry THF (10 ml) and heated at reflux for 1 hour. Na2SO4 /10H2O was added to the reaction mixture and stirred for 30 minutes. After cooling, the solids were removed by filtration and washed with THF. The filtrate was evaporated, added excess 10% HCl/MeOH and concentrated down. The resulting oil was purified by recrystallization from MeOH-Ether. The white crystal was collected by filtration and dried in vacuo to give compound 41 2HCl salt (240 mg, 0.44 mmole, 55%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. customthe solids were removed by filtration
  5. washwashed with THF
  6. customThe filtrate was evaporated
  7. additionadded excess 10% HCl/MeOH
  8. concentrationconcentrated down
  9. customThe resulting oil was purified by recrystallization from MeOH-Ether
  10. filtrationThe white crystal was collected by filtration
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8ed5bc7461fe43b39f68ead5764f521a
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716965

Notizen zur Reaktion

Wird geladen…