Chlorotrimethylsilane → (S)-tert-butyl 4-((R)-4-ethoxy-4-oxobutan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1375620

Reaktionsgleichung

Reaktionsgleichung von HRID 1375620
[Li][CH3:2].[Li+].[Br-].C[Si](Cl)(C)C.[CH2:10]([O:12][C:13](=[O:30])/[CH:14]=[CH:15]/[C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:11].[Cl-].[NH4+].[OH-].[NH4+]>C1COCC1.[Cu]I>[CH2:10]([O:12][C:13](=[O:30])[CH2:14][C@H:15]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:2])[CH3:11]

Komponenten

8

Edukt 5

HCID 6397ChlorotrimethylsilaneHCID 82050Lithium BromideHCID 10732902(S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylateHCID 21863491Ammonium chloride ammonium hydroxideHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 11336032(S)-tert-butyl 4-((R)-4-ethoxy-4-oxobutan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To CuI (3.36 g, 17.64 mmol) in THF (15 mL) was added at −78° C. MeLi.LiBr (1.5M in ether, 23.5 mL, 35.28 mmol), and the resulting mixture was stirred at −78° C. for 15 min. TMSCl (1.52 mL, 17.64 mmol) and Me2CuLi (generated above) were added in sequence at −78° C. to (S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate (0.88 g, 2.94 mmol), and the resulting mixture was slowly warmed up to rt. Ammonium chloride-ammonium hydroxide buffer (pH˜8) was added to the reaction mixture. The mixture was extracted with ether, washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, 2:8=ethyl acetate:hexanes) gave (S)-tert-butyl 4-((R)-4-ethoxy-4-oxobutan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate as a clear oil.

Aufarbeitung

  1. extractionThe mixture was extracted with ether
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09d7f4c660e34de0831918b7c835cf55
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169795B2

Verknüpfte Notizen

Wird geladen…