1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

Base Information

Chemical Name:1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid
CAS No.:190954-35-9
Molecular Formula:C₁₆H₁₈FNO₄
Molecular Weight:307.322
Hs Code.:

Synonyms:1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

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Chemical Property of 1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

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Technology Process of 1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

There total 10 articles about 1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid 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: 98.0%

: 190954-34-8
ethyl 1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylate

: 190954-35-9
1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

Guidance literature:: With sodium hydroxide; In ethanol; at 40 ℃;
DOI:10.1021/jm020328y

Reference yield:

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

: 190954-35-9
1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

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: 89 percent / Lawesson's reagent / benzene / 3 h / Heating

6.1: 95 percent / Raney Ni W-6 / ethanol / 1 h / 20 °C

7.1: 89 percent / CH₂Cl₂ / 15 h / 40 °C

8.1: 98 percent / aq. NaOH / ethanol / 40 °C

With Lawessons reagent; sodium hydroxide; 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:

: 181941-61-7
ethyl 3-(1-ethoxycarbonylcyclopropan-1-yl)-3-hydroxybutanoate

: 190954-35-9
1-[(3S,4R)-1-benzyloxycarbonyl-4-fluoropyrrolidin-3-yl]cyclopropanecarboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: SOCl₂; pyridine / 3 h / -10 °C

2.1: 56.6 g / DBU / CH₂Cl₂ / 18 h / 20 °C

3.1: NBS; AIBN / CCl₄ / 5 h / Heating

4.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

5.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

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

6.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

7.1: 89 percent / Lawesson's reagent / benzene / 3 h / Heating

8.1: 95 percent / Raney Ni W-6 / ethanol / 1 h / 20 °C

9.1: 89 percent / CH₂Cl₂ / 15 h / 40 °C

10.1: 98 percent / aq. NaOH / ethanol / 40 °C

With Lawessons reagent; pyridine; sodium hydroxide; N-Bromosuccinimide; thionyl chloride; 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