StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisobutylaluminum hydride → (S)-tert-butyl 4-((R)-5-hydroxy-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 218411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 218411
C([O:5][C:6](=O)[CH2:7][CH2:8][C@@H:9]([CH2:25][O:26][S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(C)(C)C.CC(C[AlH]CC(C)C)C.[BH4-].[Na+]>C(Cl)Cl>[OH:5][CH2:6][CH2:7][CH2:8][C@@H:9]([CH2:25][O:26][S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:28])=[O:29])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:16])([CH3:17])[N:12]1[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14487Diisobutylaluminum hydrideHCID 4311764Sodium borohydrideHCID 59201330(S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 58011504(S)-tert-butyl 4-((R)-5-hydroxy-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (317 mg, 0.58 mmol) in anhydrous DCM (8 mL) at −78° C. under N2 was added DiBAlH (1 M in hexane, 1.75 mL, 1.75 mmol) dropwise. After the addition, the reaction mixture was stirred for another 30 min. The reaction was quenched with MeOH (2 mL), followed by 50% Rochelle's salt aq solution and stirred 2 hr. The resulting solution was extracted with DCM (3×20 mL), the combined organic phases were concentrated and dissolved in THF/MeOH (10 mL, 4/1, v/v), and chilled to 0° C., NaBH4 (11 mg, 0.29 mmol) was added and stirred at this temperature for 30 min. The reaction was quenched by aqueous NH4Cl, then extracted with EtOAc (3×20 mL), the combined organic phases were washed with H2O, brine, and dried over Na2SO4, and filtered, and concentrated to give crude product (S)-tert-butyl 4-((R)-5-hydroxy-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (255 mg, 92%). It was used without further purification.

Aufarbeitung

  1. additionAfter the addition
  2. customThe reaction was quenched with MeOH (2 mL)
  3. stirringstirred 2 hr
  4. extractionThe resulting solution was extracted with DCM (3×20 mL)
  5. concentrationthe combined organic phases were concentrated
  6. dissolutiondissolved in THF/MeOH (10 mL, 4/1
  7. stirringstirred at this temperature for 30 min
  8. customThe reaction was quenched by aqueous NH4Cl
  9. extractionextracted with EtOAc (3×20 mL)
  10. washthe combined organic phases were washed with H2O, brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3cc86aff873f49f995579834d00f8c92
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198453B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion