3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)- → HCID 10946477, Verbindung

HRID 238572

Reaktionsgleichung

Reaktionsgleichung von HRID 238572
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[O:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([Si](C)(C)C)([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][C:9]1([CH3:16])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:12]([CH:13]([OH:14])[C:18]([F:20])([F:19])[F:17])[CH2:11][O:10]1

Komponenten

6

Edukt 3

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Produkt 1

HCID 10946477HCID 10946477, VerbindungAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724141Tetrabutylammonium FluorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g, 4.36 mmol), (trifluoromethyl)trimethylsilane (2.0 M solution in THF, 2.6 mL, 5.20 mmol) in THF (10 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF, 0.1 mL, 0.10 mmol) at 0° C. After addition, the mixture was stirred at room temperature for 60 h. Then, tetrabutylammonium fluoride (1.0 M solution in THF, 9 mL, 9.0 mmol) was added and the mixture stirred for another 6 h and subsequently quenched by adding saturated aq. NaHCO3 solution, extracted with EtOAc. The extracts were washed with saturated aq. NaHCO3 solution, water, brine and dried over Na2SO4. Concentration and purification gave (S)-tert-butyl 2,2-dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)oxazolidine-3-carboxylate (1.21 g, 92%), which showed a complicated NMR spectrum because of the different comformers.

Aufarbeitung

  1. additionAfter addition
  2. stirringthe mixture stirred for another 6 h
  3. customsubsequently quenched
  4. additionby adding saturated aq. NaHCO3 solution
  5. extractionextracted with EtOAc
  6. washThe extracts were washed with saturated aq. NaHCO3 solution, water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration and purification

Quellen und Nachweise

ORD-Eintrag
ord-93324d6f5b2344c5b14a673db5d4e78e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642632B2

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