Azide → (1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

HRID 527010

Reaktionsgleichung

Reaktionsgleichung von HRID 527010
[N-]=[N+]=[N-].[N:4]([C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])([CH3:13])[C@@H:8]1[OH:22])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:4][C@H:7]1[CH2:12][CH2:11][CH2:10][C@:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])([CH3:13])[C@@H:8]1[OH:22]

Komponenten

6

Edukt 3

HCID 33558AzideHCID 86667433(1R,2R,3S)-3-azido-1-(tert-butyldimethylsilyloxy)-1-methylcyclo-hexan-2-olHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68007680(1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of azide, 50d, (0.25 g; 0.89 mmol) in 20 mL of ethyl acetate was hydrogenated with Degussa palladium (20 mole %) under 1 atmosphere of hydrogen overnight. The reaction mixture was filtered over celite and the celite was eluted with 2×10 mL of EtOAc. The filtrate was concentrated in vacuo to afford 230 mg of an oil that was used directly for the next step without further purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe celite was eluted with 2×10 mL of EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08b25f2b51ec4353bc9e5b903ef312f3
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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