ChemicalBook CAS DataBase List ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-(((S)-oxiran-2-yl)methoxy)phenyl)propanoate

((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-(((S)-oxiran-2-yl)methoxy)phenyl)propanoate synthesis

5synthesis methods

Product Name:((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-(((S)-oxiran-2-yl)methoxy)phenyl)propanoate
CAS Number:144256-12-2
Molecular formula:C18H24O6
Molecular Weight:336.38

51594-55-9
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(4S)-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4- hydroxybenzene) propanoic acid,methyl ester (Landiolol)

144256-11-1
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((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-(((S)-oxiran-2-yl)methoxy)phenyl)propanoate

144256-12-2
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Yield:144256-12-2 93%

Reaction Conditions:

with tetrabutylammomium bromide;potassium carbonate in acetone;Reflux;Reagent/catalyst;

Steps:

1.2 (2) Formula II Synthesis of 4S- (2,2- dimethyl-1,3-dioxolane-4-yl) - (4- (2S, 3- propylene oxide) phenyl) propyl

Intermediate I 5.60g, Anhydrous potassium carbonate 5.53 g, Triethylbutylammonium bromide 272 mg was added to a 100 mL three-necked flask, Add 45 mL of solvent acetone, Heating up to reflux, Stirring 0.5h, A solution of (R)- epichlorohydrin (9.25 g) TLC monitors the progress of the reaction, Continue to react for 6 to 6.5 hours; After completion of the reaction, the mixture was cooled to room temperature, filter, The filter cake was rinsed with a small amount of acetone (3 mL x 3) The filtrate was concentrated, The residue was dissolved with ethyl acetate, Washed sequentially with saturated NaHCO3 solution (40 mL x 1), saturated NaCl wash solution (40 mL x 2) 3 g of anhydrous sodium sulfate for 3 hours; filter, The solvent was concentrated under reduced pressure to give the compound of formula II, 6.26 g of a pale yellow oil, The yield was 93.0%.

References:

CN106608863,2017,A Location in patent:Paragraph 0080; 0090; 0091; 0105; 0106; 0120; 0121