Benzyl Alcohol → (R)-N-Cbz-2,6-dimethyl-5-hepten-1-amine
Reaktionsgleichung
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C(O)(=O)[CH2:19][C@@H:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:21].C([N:32]([CH2:35]C)CC)C.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:21][C@H:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])[CH2:19][NH:32][C:35]([O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:8]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Diphenylphosphoryl azide (14 mL, 65 mmol) was added dropwise to a solution of (R)-citronellic acid (10 g, 59 mmol) and triethylamine (9.1 mL, 65mmol) in 60 mL of toluene. The mixture was heated for 1 hr at 80° C. 12 mL (120 mmol) of benzyl alcohol was added and the mixture was heated to reflux for 4 hrs. The reaction mixture was cooled, diluted with ethyl acetate and washed with water, saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo to give a crude product which was purified on silica gel using 5% ethyl acetate in hexane as solvent to afford 9.8 g of the desired carbamate as a thick oil.
Aufarbeitung
- temperaturethe mixture was heated
- temperatureto reflux for 4 hrs
- temperatureThe reaction mixture was cooled
- washwashed with water, saturated sodium chloride solution
- dry with materialAfter drying over anhydrous magnesium sulfate
- customthe solvent was removed in vacuo
- customto give a crude product which
- customwas purified on silica gel using 5% ethyl acetate in hexane as solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-ad5952ecb9cf4d2fa103276c0c41a12a
- Quelldatensatz
- uspto-grants-1997_05
- Patentnummer
- US05629322
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