Trimethylsilyl iodide → methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

HRID 475335

Reaktionsgleichung

Reaktionsgleichung von HRID 475335
[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[N:11](C(OC)=O)[C@H:10]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][CH2:8]1)([CH3:4])[CH3:3].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[NH:11][C@H:10]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][CH2:8]1)([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 11161884dimethyl(2S,5R)-5-((trimethylsilyl)ethynyl)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 16090847methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of dimethyl(2S,5R)-5-((trimethylsilyl)ethynyl)pyrrolidine-1,2-dicarboxylate (5.43 g, 19.16 mmol) and iodotrimethylsilane (3 mL, 28.74 mmol) in chloroform (100 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 226 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure and flash
  2. customchromatographed with 35% ethyl acetate/65% hexane

Quellen und Nachweise

ORD-Eintrag
ord-536aa212691d4fbf9e505858ef135f9e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637546B2

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