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Diethyl P-(1-phenylethyl)phosphonate → (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911504
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1911504
CCOP(OCC)([CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])=O.C([Li])CCC.[C:22]([O:26][C:27]([N:29]1[C@@H:33]([CH:34]=O)[CH2:32][O:31][C:30]1([CH3:37])[CH3:36])=[O:28])([CH3:25])([CH3:24])[CH3:23]>COCCOC>[C:22]([O:26][C:27]([N:29]1[C@@H:33](/[CH:34]=[C:6](/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)\[CH3:7])[CH2:32][O:31][C:30]1([CH3:36])[CH3:37])=[O:28])([CH3:25])([CH3:23])[CH3:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 99789Diethyl P-(1-phenylethyl)phosphonateHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418339Butyllithium

Produkt 1

HCID 68710162(S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-Dimethoxyethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of diethyl 1-phenylethyl phosphonate (2.35 ml) in 1,2-dimethoxyethane (15 ml) was cooled under an argon atmosphere to 0° C. and treated dropwise with an n-butyllithium solution (5.9 ml; 1.6 M in hexane). The reaction mixture was stirred for 5 min at 0° C., then treated dropwise with a solution of (R)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.5 g) in 1,2-dimethoxyethane (15 ml). The solution was warmed to r.t., then refluxed overnight. After cooling to r.t., the mixture was quenched with water and extracted with EtOAc. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was isolated by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 1:1) to give (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (720 mg) as light yellow viscous oil.

Aufarbeitung

  1. temperatureThe solution was warmed to r.t.
  2. temperaturerefluxed overnight
  3. temperatureAfter cooling to r.t.
  4. customthe mixture was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe crude product was isolated by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c2e25b2159f046ce957ed7b3d4573e1e
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08604061B2

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