Water → (2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic acid 1-ethylpyrrolidin-3-yl ester
Reaktionsgleichung
[CH:1]1([C@@:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([N:19]1[CH2:23][CH2:22][CH:21](O)[CH2:20]1)[CH3:18].O>CN(C=O)C>[CH2:17]([N:19]1[CH2:23][CH2:22][CH:21]([O:8][C:7](=[O:9])[C@:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)([OH:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:20]1)[CH3:18]Komponenten
Versuchsvorschrift
0.655 g (0.00297 mol) of (2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic acid were dissolved in 8 ml of dry DMF. To this solution 0.580 g (0.0036 mol) of 1,1′-carbonildiimidazol were added and the mixture was stirred at room temperature for 1 h. After this time, the mixture obtained was added to a suspension (cooled at 0° C.) of 1-ethylpyrrolidin-3-ol (0.390 ml g, 0.0033 mol) and HNa (0.078 g, 0.0033 mol) in 4 ml of dry DMF. After stirring 15 h at room temperature the reaction mixture was treated with water and extracted three times with Et2O. The organic layers were combined, washed with water and dried. The residue was purified by silica gel column chromatography (eluent: CHCl3 plus isopropanol 0%→5%) to obtain 610 mg (65%) of the title product as an oil.
Aufarbeitung
- customAfter this time, the mixture obtained
- stirringAfter stirring 15 h at room temperature the reaction mixture
- extractionextracted three times with Et2O
- washwashed with water
- customdried
- customThe residue was purified by silica gel column chromatography (eluent: CHCl3 plus isopropanol 0%→5%)
Quellen und Nachweise
- ORD-Eintrag
- ord-9b5f7d1db6184f36aa6c8043603753a3
- Quelldatensatz
- uspto-grants-2007_03
- Patentnummer
- US07192978B2
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