tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate
CAS No.:1269434-52-7
Molecular Formula:C₃₄H₄₂N₄O₄
Molecular Weight:570.732
Hs Code.:

Synonyms:tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

There total 8 articles about tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate 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:

: 1269429-09-5
tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

: 1269434-52-7
tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran

2: sodium hydroxide / tetrahydrofuran; water; methanol

3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2016.12.033

Reference yield:

: 1190391-62-8
(2R)-2-[(S)-hydroxy(phenyl)methyl]hex-5-ynoic acid

: 1269434-52-7
tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile

2.1: triethylamine; diphenylphosphoranyl azide / toluene / 110 °C

3.1: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; caesium carbonate / acetonitrile / 50 °C

4.1: trifluoroacetic acid / dichloromethane

5.1: palladium diacetate / toluene / 80 °C

5.2: 2585.81 Torr

6.1: triethylamine / dichloromethane

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran

8.1: sodium hydroxide / tetrahydrofuran; water; methanol

9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; palladium diacetate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: |Curtius Rearrangement / 3.1: |Sonogashira Cross-Coupling;
DOI:10.1016/j.bmcl.2016.12.033

Reference yield:

: C₃₅H₄₃NO₅Si

: 1269434-52-7
tert-butyl (2R,5S)-2-[(R)-hydroxy(phenyl)methyl]-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: trifluoroacetic acid / dichloromethane

2.1: palladium diacetate / toluene / 80 °C

2.2: 2585.81 Torr

3.1: triethylamine / dichloromethane

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran

5.1: sodium hydroxide / tetrahydrofuran; water; methanol

6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

With tetrabutyl ammonium fluoride; palladium diacetate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmcl.2016.12.033