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HRID 464462Erstellt: 24. Oktober 2026

Dicyclohexylcarbodiimide → (S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate

https://huagongshe.com/de/reaction/464462

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDicyclohexylcarbodiimideHCID 10868—
Edukt(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 9837437—
Edukt(1R,cis)2,2-dimethyl-3-[2-cyclopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylic acidHCID 18599577—
Katalysator4-(Dimethylamino)pyridineHCID 14284—
LösungsmittelDichloromethaneHCID 6344—
Produkt(S)alpha-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylateHCID 13171438168,4%

Reaktionsbedingungen

Temperatur0 °C

Reaktionsschritte

2.96 g of dicyclohexylcarbodiimide were added at 0° C. to a stirred mixture of 3.6 g of the product of Step B, 30 ml of methylene chloride and 30 mg of 4-dimethylaminopyridine followed by the addition of a solution of 3.3 g of (S)α-cyano-3-phenoxy-benzyl alcohol in 10 ml of methylene chloride. The mixture was stirred at 0° C. for 5 minutes and at 20°-25° C. for 3 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a cyclohexane-ethyl acetate mixture yielded 4.5 g of (S)α-cyano-3-phenoxybenzyl(1R,cis)2,2-dimethyl-3-[2-(cyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate with a melting point of =72° C.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04547522
Quelldatensatzuspto-grants-1985_10
ORD IDord-35cc5308e291490b9e64da0d0b9a6f79
Quellennotizuspto-grants-1985_10