Reaktionsgleichung
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([CH3:19])(O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-:21].[K+].[K+].[C:26](#[N:28])[CH3:27]>>[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([NH:28][C:26](=[O:21])[CH3:27])([CH3:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Komponenten
Versuchsvorschrift
Add concentrated sulphuric acid (16 mL) dropwise to 1-benzyl-3-methyl-pyrrolidin-3-ol (4.4 g, 23 mmol) in acetonitrile (12 mL) at 0° C. Stir and allow the resulting solution to warm up gradually to room temperature overnight. Pour onto crushed ice and add saturated aqueous potassium carbonate and extract with dichloromethane. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give N-(1-benzyl-3-methylpyrrolidin-3-yl)-acetamide which may be used in the next step without further purification (4.89 g, 70%). 1H NMR (400 MHz, CDCl3) δ 7.22-7.34 (5H, m), 5.62 (1H, s), 3.57-3.66 (2H, m), 2.76-2.84 (2H, m), 2.54 (1H, td, J=8.80, 5.87 Hz), 2.47 (1H, d, J=9.78 Hz), 2.13 (1H, m), 1.90-1.93 (3H, m), 1.84-1.90 (1H, m), 1.49 (3H, s), MS (ES): m/z=233 [M+H].
Aufarbeitung
- additionPour
- customonto crushed ice
- extractionextract with dichloromethane
- washwash with saturated aqueous sodium chloride
- dry with materialdry (magnesium sulfate)
- concentrationconcentrate
Quellen und Nachweise
- ORD-Eintrag
- ord-84ce6ce6bac146bb9fcaaa2cd5080ec9
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07868014B2
Verknüpfte Notizen
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