(1R,2R)-ethyl2-(3,4-difluorophenyl)cyclopropane carboxylate Chemical Properties

Boiling point:

262.7±40.0 °C(Predicted)

Density 

1.257±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

(1R,2R)-ethyl2-(3,4-difluorophenyl)cyclopropane carboxylate Usage And Synthesis

Uses

(1R,2R)-trans-Ethyl 2-(3,4-difluorophenyl)cyclopropanecarboxylate is a useful chemical in studying the inhibitory effect on ADP-induced platelet aggregation of ticagrelor derivatives as antiplatelet agents.

Synthesis

The general procedure for the synthesis of ethyl (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate from triethyl phosphonoacetate and (S)-2-(3,4-difluorophenyl)oxirane was as follows: sodium tert-butoxide (115.2 g, 1.2 mol) and triethyl phosphonoacetate (269.0 g, 1.2 mol) with toluene (150 g) were added to a 2 L three-necked flask and heated to 100 °C. Subsequently, a toluene solution of (S)-2-(3,4-difluorophenyl)oxirane was slowly added dropwise, and the reaction temperature was controlled to be maintained at 100 °C, and the reaction lasted for 4 hours. After completion of the reaction, the reaction mixture was cooled and quenched by addition of water (500 g). The organic phase was separated, dried with anhydrous sodium sulfate and concentrated to afford the target product ethyl (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate 203.9 g in 90.6% yield, 99.2% ee value and 99.2% purity.

References

[1] Patent: CN107686447, 2018, A. Location in patent: Paragraph 0024; 0029; 0030; 0034
[2] Patent: WO2008/18823, 2008, A1. Location in patent: Page/Page column 30
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3598 - 3602

(1R,2R)-ethyl2-(3,4-difluorophenyl)cyclopropane carboxylate(1006376-61-9)Related Product Information

• (trans)-2-(3,4-difluorophenyl)cyclopropanecarboxamide
• Ticagrelor Sulfone
• Ticagrelor Related Compound 15
• Ticagrelor Related Compound 3 ((+/-)-6-Aminotetrahydro-2,2-Dimethyl-4H-Cyclopenta-1.3-dioxol-4-ol)
• Ticagrelor Related Compound 38D-Tartrate
• Ticagrelor Related Compound 90 HCl
• 2-[[(3aS,4R,6S,6aR)-4-[7-[[(1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl]amino]-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]oxy]ethanol
• 2-(Propylthio)-4(1H)-pyrimidinone
• Ticagrelor diastereoMer
• Ticagrelor Sulphone
• Ticagrelor Related Compound 14
• 4-Chloro-2-propylsulfanyl-pyrimidine
• 2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol
• Ticagrelor iMpurity
• 4,6-DICHLORO-5-NITRO-2-PROPYLTHIOPYRIMIDINE
• Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-aMino-6-chloro-2-(propylthio)-4-pyriMidinyl]aMino]tetrahydro-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-
• N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester
• AR-C 124910XX