反应详情

温度

-10 °C

A stirred solution of thionyl chloride (0.14 ml, 1.91 mMol) in acetonitril (10 ml) is cooled to −40° C. At this temperature, a solution of [(R)-3-(4-heptyloxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester (300 mg, 0.76 mMol) in acetonitril (5 ml), and pyridine (0.31 ml, 3.81 mMol) are added successively. The mixture is allowed to warm to −10° C. over 2.5 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and HCl (aqueous, 1 M). The aqueous phase is extracted twice with AcOEt. The combined organic layers are washed with NaHCO3 (saturated aqueous solution), dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 5%→15% AcOEt in heptane gives the title compounds as colourless oils (2 diastereomers, dr=1:1).

1. extractionThe aqueous phase is extracted twice with AcOEt
2. washThe combined organic layers are washed with NaHCO3 (saturated aqueous solution)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. washColumn chromatography eluting with 5%→15% AcOEt in heptane