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

Temperatur

-78 °C

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.

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

ORD-Eintrag

ord-a1d21d4534b24d32af958e1968bffb56

Quelldatensatz

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07928093B2