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

HRID 2039926
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2039926
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 (1M 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-08727e1eed1c49e4b45696639b551c7e
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580823B2

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