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Lithium Chloride → Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 227566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 227566
[BH4-].[Na+].[Li+].[Cl-].C[O:6][C:7]([CH:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O>CCO.C1COCC1>[C:19]([O:18][C:16]([N:10]1[CH:9]([CH2:7][OH:6])[CH2:13][O:12][C:11]1([CH3:15])[CH3:14])=[O:17])([CH3:22])([CH3:21])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 51384973-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

Produkt 1

HCID 14409442Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of NaBH4 (2.247 g, 59.08 mmol) and LiCl (2.505 g, 59.08 mmol) in EtOH (42 mL), stirring under nitrogen at 0° C., was added (35) (7.659 g, 29.54 mmol) in THF (30 mL) dropwise. This mixture was allowed to warn to room temperature and continued stirring for 48 hours. The precipitate was filtered and washed with ethanol. The washings were concentrated and extracted with EtOAc. The organic layer was then washed with brine and dried over anhydrous Na2SO4. Column chromatography on SiO2 (1:1 EtOAc/Hexanes) was utilized to purify 6.101 g (89%) of the title compound as a white solid.

Aufarbeitung

  1. customto warn to room temperature
  2. stirringcontinued stirring for 48 hours
  3. filtrationThe precipitate was filtered
  4. washwashed with ethanol
  5. concentrationThe washings were concentrated
  6. extractionextracted with EtOAc
  7. washThe organic layer was then washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customto purify 6.101 g (89%) of the title compound as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-018d7a518f2c4a5cabd26bc13a623460
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560477B2

Notizen zur Reaktion

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