ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

Base Information

Chemical Name:ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate
CAS No.:190954-46-2
Molecular Formula:C₁₈H₂₂FNO₄
Molecular Weight:335.375
Hs Code.:

Synonyms:ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

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Chemical Property of ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

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Technology Process of ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

There total 10 articles about ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 190954-45-1
ethyl 1-{(3S,4SR)-4-fluoro-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate

: 190954-46-2
ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

Guidance literature:: In dichloromethane; at 40 ℃;
DOI:10.1021/jm020328y

Reference yield:

: 181941-62-8
ethyl (E)-3-(1-ethoxycarbonylcyclopropan-1-yl)-2-butenoate

: 190954-46-2
ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NBS; AIBN / CCl₄ / 5 h / Heating

2.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

3.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

4.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

5.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

5.2: 74 percent / 2,6-di-t-butylphenol / tetrahydrofuran

6.1: 90 percent / Lawesson's reagent / benzene / Heating

7.1: 86 percent / Raney Ni W-6 / ethanol / 20 °C

8.1: 89 percent / CH₂Cl₂ / 40 °C

With Lawessons reagent; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; hydrogen; sodium hydrogencarbonate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; benzene;
DOI:10.1021/jm020328y

Reference yield:

: 1-(1-chloro-2-ethoxycarbonyl-1-methyl-ethyl)-cyclopropanecarboxylic acid ethyl ester

: 190954-46-2
ethyl 1-[(3S,4SR)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 56.6 g / DBU / CH₂Cl₂ / 18 h / 20 °C

2.1: NBS; AIBN / CCl₄ / 5 h / Heating

3.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

4.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

5.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

5.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

6.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

6.2: 74 percent / 2,6-di-t-butylphenol / tetrahydrofuran

7.1: 90 percent / Lawesson's reagent / benzene / Heating

8.1: 86 percent / Raney Ni W-6 / ethanol / 20 °C

9.1: 89 percent / CH₂Cl₂ / 40 °C

With Lawessons reagent; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; benzene;
DOI:10.1021/jm020328y