ChemicalBook CAS DataBase List (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE

(4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE synthesis

9synthesis methods

Product Name:(4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE
CAS Number:85416-75-7
Molecular formula:C16H21NO3
Molecular Weight:275.34

(E)-2-(cyclopentyloxy)-1-methoxy-4-(2-nitrovinyl)benzene

141332-74-3
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108-59-8 Synthesis

108-59-8
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(4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE

85416-75-7
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$74.00/1mg

85416-73-5 Synthesis

85416-73-5
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Yield: 87 % ee

Reaction Conditions:

with C₃₃H₃₂F₆N₄O₃;sodium chloride in water;toluene at 20; for 24 h;Overall yield = 95 %; enantioselective reaction;Reagent/catalyst;Solvent;

Steps:

1 Example 1:Chiral (R) mixture in a mixed medium of an organic solvent to the aqueous solution preparation of the precursor Rolipram
Thechiral catalyst 0.10 mmol shown in terms of the malonate 5.0 mmol shown interms of 3 - (cyclopentoxy) -4- methoxy phenyl night shown in terms of thechemical formula 2 in the alkyne 1.0 mmol, and the chemical formula 7, and thechemical formula 6 was stirred in the mixed solvent of the saturation sodiumchloride aqueous solution (saturated sodium chloride aqueous solution) 2.0 mLdepartment toluene 0.2 mL of 20 for 24 hours. Thereaction mixture the solvent was removed using the dichloromethane(CH(sub)2(/sub)Cl(sub)2(/sub)) solvent after doing the extraction under thereduced pressure and the product was separated after the stirring end using thecolumn chromatography and the chirality (R) - rolipram precursor was obtained(95% yield). (R)- , (enantiomeric excess) (CHIRALCEL AD-H, 90:10,:, 210 nm, 1.0 ml/, t()=19.7, t()=42.2, 87% ee, (R)-form). Themanufactured chirality (R) - rolipram precursor the enantiomeric excess wasmeasured using the high effectiveness liquid chromatography (the CHIRALCELAD-H, 90:10, hexane isopropyl alcohol, 210 nm, 1.0 ml /, T (major product)=19.7 minute, T (by-product) =42.2 minute, 87% ee, (R) -form).

References:

Sungkyunkwan University Academic Cooperation;Song, Chung Uii;Bae, Han Yong;Jung, Ji Yun KR101548886, 2015, B1 Location in patent:Paragraph 0072-0074