Reaktionsgleichung
[C:1]([N:5]1[C:10](=[O:11])[CH:9]2[CH2:12][CH:6]1[CH:7]=[CH:8]2)(=[O:4])[CH2:2][CH3:3].CC(O)CC.[BH4-].[Na+].Cl>O>[C:1]([NH:5][CH:6]1[CH2:12][CH:9]([CH2:10][OH:11])[CH:8]=[CH:7]1)(=[O:4])[CH2:2][CH3:3]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
16.6 g of (±)-2-propionyl-2-azabicyclo[2.2.1]-hept-5-en-3-one were dissolved in water (140 ml) and 2-butanol (66 ml) under nitrogen and cooled to −5° C. 3 g of sodium borohydride were added in portions over the course of 2 h. The mixture was stirred at 10° C. for 2.5 h and then adjusted to pH 2.2 with a mixture of conc. hydrochloric acid and water (1/1). The solution was evaporated to 40 g and adjusted to pH 6.2 with 2N NaOH. The mixture was extracted with 5×50 ml of dichloromethane. The combined organic phases were completely evaporated, and the residue was recrystallized in toluene (150 ml). 11.1 g of title compound were obtained. The yield was 65%.
Aufarbeitung
- customThe solution was evaporated to 40 g
- extractionThe mixture was extracted with 5×50 ml of dichloromethane
- customThe combined organic phases were completely evaporated
- customthe residue was recrystallized in toluene (150 ml)
Quellen und Nachweise
- ORD-Eintrag
- ord-984dbd0900c346018b339a956e791d8c
- Quelldatensatz
- uspto-grants-2008_07
- Patentnummer
- US07405065B2
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