Water → HCID 178484843, Verbindung

HRID 590378

Reaktionsgleichung

Reaktionsgleichung von HRID 590378
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=O)OC(C)(C)C)[CH2:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:15][NH:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([OH:7])[CH2:9][CH2:10]1

Komponenten

7

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178418329HCID 178418329, Verbindung2×

Produkt 1

HCID 178484843HCID 178484843, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of lithium aluminium hydride (9 g, 0.23 mol) in tetrahydrofuran (425 mL) was added slowly tert-butyl (trans-4-hydroxycyclohexyl)carbamate (intermediate 1, 10 g, 0.046 mol). The mixture was refluxed overnight. Once the mixture was cooled to room temperature, 9 ml of water, 9 ml of 4N NaOH solution and 18 ml of water were carefully and successively dropped. The organic solvent was removed under reduced pressure and the crude obtained was dissolved with chloroform and dried over magnesium sulphate. The filtrate was evaporated to dryness and co evaporated with hexane to give the title compound as a white solid (89%). This intermediate is also described in JMC, 1987, 30(2), p 313.

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. additionsuccessively dropped
  3. customThe organic solvent was removed under reduced pressure
  4. customthe crude obtained
  5. dry with materialdried over magnesium sulphate
  6. customThe filtrate was evaporated to dryness and co
  7. customevaporated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-41e511a820cf49698d5b30af83656bec
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233108B2

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