rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol → rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

HRID 245067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245067
[N:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@:5]1([CH3:28])[OH:27])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:25])([CH3:24])[CH3:26])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@:5]1([CH3:28])[OH:27]

Komponenten

4

Edukt 1

HCID 86693778rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

Produkt 1

HCID 86693777rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanolAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol (2.28 g, 5.76 mmol, enantiomeric mixture) and 10% palladium on carbon (61 mg) in ethanol (29 mL) is hydrogenated (60 psi) at room temperature for 16 h. The reaction is filtered through a pad of diatomaceous earth and rinsed with EtOH (50 mL). The filtrate is concentrated in vacuo, dissolved in dichloromethane (10 mL), and concentrated in vacuo. The crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane) to afford the title compound as an opaque yellow oil (419 mg, 20%). LC-ES/MS m/z 353 (M+1).

Aufarbeitung

  1. customat room temperature
  2. customfor 16 h
  3. filtrationThe reaction is filtered through a pad of diatomaceous earth
  4. washrinsed with EtOH (50 mL)
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutiondissolved in dichloromethane (10 mL)
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-b97ab8e8c7bb43a68dfd9e2deeb76cf8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658693B2

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