(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1185885-10-2
Molecular Formula:C₂₀H₂₇N₅O₃
Molecular Weight:385.466
Hs Code.:

Synonyms:(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 6 articles about (S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 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: 46.0%

: 1185884-96-1
5-((S)-1-tert-butoxycarbonylpyrrolidin-2-yl)-3H-1,2,3-triazole-4-carboxylic acid

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: 1185885-10-2
(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: 5-((S)-1-tert-butoxycarbonylpyrrolidin-2-yl)-3H-1,2,3-triazole-4-carboxylic acid; With N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃;

(R)-1-phenyl-ethyl-amine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 10.5h; optical yield given as %de;
DOI:10.1016/j.tet.2009.05.045

Reference yield:

: 130418-90-5,130495-08-8
(S)-tert-butyl 2-ethynylpyrrolidine-1-carboxylate

: 1185885-10-2
(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.92 h / -30 - 20 °C / Inert atmosphere

2.1: sodium azide; ammonium chloride / dimethyl sulfoxide / 1.33 h / 100 °C / Sealed tube

3.1: 20 % Pd(OH)2/C; hydrogen / methanol; ethyl acetate / 0.83 h / 20 °C

4.1: N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 °C

4.2: 10.5 h / 0 - 20 °C

With n-butyllithium; sodium azide; N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate; 20 % Pd(OH)2/C; hydrogen; ammonium chloride; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2009.05.045

Reference yield:

: 1185884-92-7
(S)-1-tert-butoxycarbonylpyrrolidin-2-yl-propynoic acid ethyl ester

: 1185885-10-2
(S)-2-(5-((R)-1-phenylethylcarbamoyl)-1H-1,2,3-triazol-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium azide; ammonium chloride / dimethyl sulfoxide / 3.33 h / 100 °C

2.1: water; lithium hydroxide / tetrahydrofuran / 0 °C / Reflux

2.2: 20 °C

3.1: N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 °C

3.2: 10.5 h / 0 - 20 °C

With sodium azide; N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate; water; ammonium chloride; lithium hydroxide; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2009.05.045