ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

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Chemical Name:ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate
CAS No.:190954-44-0
Molecular Formula:C₁₈H₂₂FNO₂S
Molecular Weight:335.443
Hs Code.:

Synonyms:ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

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Chemical Property of ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

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Technology Process of ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

There total 9 articles about ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-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: 90.0%

: 190954-43-9
ethyl 1-{(3S,4S)-4-fluoro-5-oxo-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate

: 190954-44-0
ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

Guidance literature:: With Lawessons reagent; In benzene; Heating;
DOI:10.1021/jm020328y

Reference yield:

: 2627-86-3
(S)-1-phenyl-ethylamine

: 190954-44-0
ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

2.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

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

3.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

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

4.2: 74 percent / 2,6-di-t-butylphenol / tetrahydrofuran

5.1: 90 percent / Lawesson's reagent / benzene / Heating

With Lawessons reagent; hydrogen; sodium hydrogencarbonate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; benzene;
DOI:10.1021/jm020328y

Reference yield:

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

: 190954-44-0
ethyl 1-{(3S,4S)-4-fluoro-1-[(S)-1-phenylethyl]-5-thioxopyrrolidin-3-yl}cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 6 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

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