5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

Base Information

Chemical Name:5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid
CAS No.:1356491-83-2
Molecular Formula:C₂₃H₂₈N₂O₅
Molecular Weight:412.486
Hs Code.:

Synonyms:5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

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Chemical Property of 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

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Technology Process of 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

There total 11 articles about 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic 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: 96.0%

: 1356491-88-7
methyl 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylate

: 1356491-83-2
5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

Guidance literature:: methyl 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylate; With water; sodium hydroxide; In tetrahydrofuran; methanol; at 60 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; water; pH=6.5;

Reference yield:

: 53293-00-8
hex-5-ynoic acid

: 1356491-83-2
5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 2.33 h / -25 °C / Inert atmosphere

1.2: 20 °C

2.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 - 5 °C

3.2: pH 3

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

4.2: 1.5 h

4.3: pH 3

5.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

5.2: 16 h / 105 °C

6.1: triethylamine / copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 5 h / 55 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

8.1: palladium diacetate / toluene / 5 h / 80 °C / Inert atmosphere

8.2: 16 h / 2585.81 Torr

9.1: triethylamine / tetrahydrofuran / 20 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C

11.2: pH 6.5

With chloro-trimethyl-silane; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; sodium hydroxide; magnesium chloride; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

Reference yield:

: 1190391-59-3
(S)-3-(hex-5-ynoyl)-4-phenyloxazolidin-2-one

: 1356491-83-2
5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 - 5 °C

2.2: pH 3

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

3.2: 1.5 h

3.3: pH 3

4.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

4.2: 16 h / 105 °C

5.1: triethylamine / copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 5 h / 55 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

7.1: palladium diacetate / toluene / 5 h / 80 °C / Inert atmosphere

7.2: 16 h / 2585.81 Torr

8.1: triethylamine / tetrahydrofuran / 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C

10.2: pH 6.5

With chloro-trimethyl-silane; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; sodium hydroxide; magnesium chloride; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile;