Water → HCID 178484843, Verbindung

HRID 25534

Reaktionsgleichung

Reaktionsgleichung von HRID 25534
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:15](=O)[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1)C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Na+].[Na+].O>C1COCC1>[CH3:15][NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178523817HCID 178523817, Verbindung

Produkt 1

HCID 178484843HCID 178484843, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 37.9 g (0.94 mol, 2.0 eq) LAH in 1.3 l THF was added a suspension of 117 g (0.47 mol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester in 11 THF over a period of 6 h via a cannula keeping the temperature between 5-10° C. The reaction was refluxed over night and a mixture of Na2SO4, silica gel and water (160 g, 50 g, 80 ml) was added, stirred for additional 30 min, filtered and concentrated. The crude material was titurated with hexane to yield 27.9 g (46%) trans-4-Methylamino-cyclohexanol. Column chromatography of the mother liquor on silica gel yielded additional 17.1 g (28%) trans-4-Methylamino-cyclohexanol as white solid, MS: 129 (MH+) (in analogy to Venuti, Michael C.; Jones, Gordon H.; Alvarez, Robert; Bruno, John J.; J.Med.Chem.; 30; 2; 1987; 303-318).

Aufarbeitung

  1. additionwas added
  2. custombetween 5-10° C
  3. temperatureThe reaction was refluxed over night
  4. additionwas added
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-48fa585817f74c2fa874d0d25871e2e2
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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