(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane → (+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

HRID 1243168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243168
[N:1]([C@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:5]1)=[N+]=[N-].[H][H]>C(O)C.[Pt]=O>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][C@H:6]1[CH2:7][CH2:8][C@H:4]([NH2:1])[CH2:5]1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 2

HCID 21062583(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silaneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 58715071(+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (±)-trans-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane (400 mg, 1.66 mmol) (from Example 9b supra) and platinum oxide (38 mg, 0.17 mmol) (Aldrich) in ethanol (6 mL) was stirred under 1 atmosphere of hydrogen pressure for 2 hours. The reaction mixture was then filtered. The solids were washed with tetrahydrofuran (approx. 40 mL) and the combined organic layer was evaporated under reduced pressure to give (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine as a colorless liquid. (Yield 270 mg, 76%).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. washThe solids were washed with tetrahydrofuran (approx. 40 mL)
  3. customthe combined organic layer was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b6eb1d08bb6c40439ddb712f6146802d
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115740B2

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