Trimethylsilylacetylene → (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one

HRID 2076795

Reaktionsgleichung

Reaktionsgleichung von HRID 2076795
[CH3:1][Si](C#C)(C)C.C([Li])CCC.[C:12]([O:16][C:17](=[O:39])[NH:18][C@:19]([CH:37]=O)(C)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1)([CH3:15])(C)C>C1COCC1>[C:15]([CH:12]1[O:16][C:17](=[O:39])[NH:18][C@@:19]1([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=1)[CH3:37])#[CH:1]

Komponenten

5

Edukt 3

HCID 66111TrimethylsilylacetyleneHCID 59339517[(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

Produkt 1

HCID 86615288(R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of trimethylsilylacetylene (0.18 ml, 1.27 mMol) in THF (18 ml) at −78° C. is added n-Butyllithium (0.49 ml, 2.5 M in cyclohexane). After 5 minutes, [(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (200 mg, 0.51 mMol) in THF (2 ml) is added and the reaction is stirred at −78° C. for 5 hours. After that time, the cooling is removed and the reaction is stirred for 16 hours at RT. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 8%-45% AcOEt in heptane gives (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one and its C5 epimer.

Aufarbeitung

  1. customAfter that time, the cooling is removed
  2. stirringthe reaction is stirred for 16 hours at RT
  3. additionThe reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution)
  4. extractionThe aqueous phase is extracted with AcOEt (3 times)
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. washColumn chromatography eluting with 8%-45% AcOEt in heptane

Quellen und Nachweise

ORD-Eintrag
ord-a1d21d4534b24d32af958e1968bffb56
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928093B2

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