Methanesulfonyl chloride → (2R,3S)-3-Hydroxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
Reaktionsgleichung
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:3]1[CH2:14][OH:15].C([Sn](CCCC)=O)CCC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1(C)C=CC=CC=1>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[C@H:3]1[CH2:14][O:15][S:27]([CH3:26])(=[O:29])=[O:28])=[O:8])([CH3:11])([CH3:12])[CH3:13]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
A suspension of (2R,3S)-tert-butyl 3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (5.04 g, 23.20 mmol) and dibutyloxostannane (7.07 g, 27.84 mmol) in toluene (50 mL) is refluxed in a 130° C. oil bath for 2 h. The mixture is cooled to 0° C. in an ice bath for 30 min and treated with methanesulfonyl chloride (2.15 mL, 27.84 mmol) at once. The reaction is stirred for 30 min at 0° C. and then the mixture allowed to gradually warm to ambient temperature overnight. The solution is concentrated and the resulting residue purified by medium pressure liquid chromatography, eluting with ethyl acetate:hexane (8:2). Fractions containing pure product are combined and concentrated to give 6.14 g (96%) of dense oil as the title compound. LC-ES/MS m/z 318.2 [M+Na]+, TR=2.34 min.
Aufarbeitung
- temperatureThe mixture is cooled to 0° C. in an ice bath for 30 min
- temperatureto gradually warm to ambient temperature overnight
- concentrationThe solution is concentrated
- customthe resulting residue purified by medium pressure liquid chromatography
- washeluting with ethyl acetate:hexane (8:2)
- additionFractions containing pure product
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-4e2e5afd2577434988251baf9d8ff4e9
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08486943B2
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