(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

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Chemical Name:(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine
CAS No.:190954-36-0
Molecular Formula:C₂₀H₂₇FN₂O₄
Molecular Weight:378.444
Hs Code.:

Synonyms:(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

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Chemical Property of (3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

Chemical Property:

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Technology Process of (3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

There total 9 articles about (3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine 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:

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

: 190954-36-0
(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

Guidance literature:: Multi-step reaction with 9 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

9.1: 65 percent / Et₃N; diphenylphosphoryl azide / Heating

With Lawessons reagent; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; benzene; 9.1: Curtius rearrangement;
DOI:10.1021/jm020328y

Reference yield:

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

: 190954-36-0
(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

Guidance literature:: Multi-step reaction with 10 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: 89 percent / Lawesson's reagent / benzene / 3 h / Heating

7.1: 95 percent / Raney Ni W-6 / ethanol / 1 h / 20 °C

8.1: 89 percent / CH₂Cl₂ / 15 h / 40 °C

9.1: 98 percent / aq. NaOH / ethanol / 40 °C

10.1: 65 percent / Et₃N; diphenylphosphoryl azide / Heating

With Lawessons reagent; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; benzene; 10.1: Curtius rearrangement;
DOI:10.1021/jm020328y

Reference yield:

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

: 190954-36-0
(3R,4R)-1-benzyloxycarbonyl-4-[1-(tert-butoxycarbonylamino)cyclopropan-1-yl]-3-fluoropyrrolidine

Guidance literature:: Multi-step reaction with 11 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

11.1: 65 percent / Et₃N; diphenylphosphoryl azide / Heating

With Lawessons reagent; pyridine; sodium hydroxide; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; benzene; 11.1: Curtius rearrangement;
DOI:10.1021/jm020328y