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Methyl iodide → (4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1697248
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1697248
[CH3:1]N(C)CCO.[Li+].CCC[CH2-].[Si:12]([O:19][CH2:20][C@H:21]1[O:25][C:24]([CH3:27])([CH3:26])[N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:22]1[CH2:35][C:36]1[CH:41]=[CH:40][N:39]=[C:38]([Cl:42])[CH:37]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].CI>C1COCC1>[Si:12]([O:19][CH2:20][C@H:21]1[O:25][C:24]([CH3:27])([CH3:26])[N:23]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C@H:22]1[CH2:35][C:36]1[CH:41]=[C:40]([CH3:1])[N:39]=[C:38]([Cl:42])[CH:37]=1)([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 79022-(Dimethylamino)ethanolHCID 61028n-Butyl lithiumHCID 86635710(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloropyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 86614126(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dimethylethanolamine (0.128 ml, 1.27 mmol) was added to anhydrous hexanes (1.4 L) and cooled to 0° C. N-BUTYLLITHIUM (2.5 M in hexanes)(1.02 ml, 2.55 mmol) was added dropwise and stirred for 30 minutes before being cooled to −78° C. (4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloropyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.200 g, 0.425 mmol) in hexanes (1 mL) was added dropwise and the solution was stirred for 1 hour at −78° C. to give a dark orange solution. MeI (0.106 ml, 1.70 mmol) in THF (3.2 mL) was added dropwise and the reaction was allowed to slowly warm to 0° C. and was quenched with saturated aqueous ammonium chloride. The reaction was diluted with ethyl acetate and water and separated. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated to give the titled compound which was used directly for the next step without purification.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringthe solution was stirred for 1 hour at −78° C.
  3. customto give a dark orange solution
  4. temperatureto slowly warm to 0° C.
  5. customwas quenched with saturated aqueous ammonium chloride
  6. additionThe reaction was diluted with ethyl acetate and water
  7. customseparated
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. washthe combined organic layers were washed with water, brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-64362959ed9c45c999fe116bd75a767e
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163909B2

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