(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

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Chemical Name:(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate
CAS No.:1374416-96-2
Molecular Formula:C₂₄H₂₇N₃O₄
Molecular Weight:421.496
Hs Code.:

Synonyms:(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

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Chemical Property of (R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

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Technology Process of (R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

There total 10 articles about (R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)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: 83.0%

: 1374416-87-1
(S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile

: 501-53-1,94274-21-2
benzyl chloroformate

: 1374416-96-2
(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

Guidance literature:: (S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile; With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 0.5h; Inert atmosphere;

benzyl chloroformate; In water; ethyl acetate; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2017.08.043

Reference yield:

: 1374416-88-2
1-benzyl-3-(2-(benzyloxy)acetyl)pyrrolidin-2-one

: 1374416-96-2
(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: [RuCl(cymene)((R)-DM-BINAP)]Cl; hydrogen / methanol / 15 h / 80 °C / 18241.2 Torr / Autoclave

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 23 °C / Reflux; Inert atmosphere

3.1: triethylamine / dichloromethane / 16 h / 0 - 23 °C

4.1: n-heptane; toluene / 15 h / 60 °C

4.2: pH 2

4.3: pH 13

5.1: hydrogenchloride; palladium on carbon; hydrogen / methanol; water / 24 h / 23 °C / 2585.81 Torr

6.1: sodium hydroxide / tetrahydrofuran / 3.17 h / 0 °C

7.1: triethylamine / dichloromethane / 0.67 h / 0 °C

8.1: tert-butyl methyl ether / 3 h / 50 °C

With hydrogenchloride; lithium aluminium tetrahydride; [RuCl(cymene)((R)-DM-BINAP)]Cl; tert-butyl methyl ether; palladium on carbon; hydrogen; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; toluene;
DOI:10.1021/jo3004716

Reference yield:

: (R)-2-(methylamino)-2-((R)-pyrrolidin-3-yl)ethanol bishydrochloride

: 1374416-96-2
(R)-benzyl 3-((S)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-cyanoethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / tetrahydrofuran / 3.17 h / 0 °C

2: triethylamine / dichloromethane / 0.67 h / 0 °C

3: tert-butyl methyl ether / 3 h / 50 °C

With tert-butyl methyl ether; triethylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo3004716