Tert-butyl 9-benzyl-7-oxo-3,9-diazabicyclo[3.3.1]nonane-3-carboxylate → 3-Boc-7-oxo-3,9-diazabicyclo[3.3.1]nonane

HRID 2354886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354886
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16](CC3C=CC=CC=3)[CH:10]([CH2:11][C:12](=[O:24])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[NH:16][CH:10]([CH2:11][C:12](=[O:24])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 59679479Tert-butyl 9-benzyl-7-oxo-3,9-diazabicyclo[3.3.1]nonane-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 596794733-Boc-7-oxo-3,9-diazabicyclo[3.3.1]nonaneAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

9-Benzyl-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (16.6 g, 50.5 mmol) was dissolved in methanol (40 mL) and added to a suspension of palladium hydroxide (1 g) in methanol (10 mL) in a Parr bottle. The Parr bottle was filled with hydrogen (40 psi) and evacuated three times. The Parr bottle was refilled with hydrogen (40 psi) and shook for 48 h. The suspension was filtered through Celite and concentrated under vacuum to give 12.1 g (quantitative yield) of 7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as a yellow oil. Retention time (min)=0.531, method [1], MS(ESI) 481.3 (2M+H).

Aufarbeitung

  1. customevacuated three times
  2. additionThe Parr bottle was refilled with hydrogen (40 psi)
  3. filtrationThe suspension was filtered through Celite
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3c8deb837c6945e38224ab9f70a9e989
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754712B2

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