Trimethylsilyl iodide → methyl (5R)-5-propenyl-L-prolinate
Reaktionsgleichung
[C:1]([C@@H:4]1[N:8](C(OC)=O)[C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)#[C:2][CH3:3].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH:1]([C@@H:4]1[NH:8][C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)=[CH:2][CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of dimethyl (2S,5R)-5-propynyl-pyrrolidine-1,2-dicarboxylate (4.25 g, 18.90 mmol) and iodotrimethylsilane (3.23 mL, 22.7 mmol, Example 85A) in chloroform (60 mL) was heated to 65° C. for 3 hours, was cooled to room temperature, concentrated under reduced pressure and flash chromatographed with 35% ethyl acetate/65% hexane to provide the titled compound. MS (DCI/NH3) m/e 168 (M+H)+.
Aufarbeitung
- concentrationconcentrated under reduced pressure and flash
- customchromatographed with 35% ethyl acetate/65% hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-dbce47a10b434b0084326f1bf82d164e
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08119664B2
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