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

Base Information

Chemical Name:(R)-benzyl 3-((R)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxyethyl)pyrrolidine-1-carboxylate
CAS No.:1374416-95-1
Molecular Formula:C₂₃H₂₈N₂O₅
Molecular Weight:412.486
Hs Code.:

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

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

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

There total 5 articles about (R)-benzyl 3-((R)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxyethyl)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: 80.0%

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

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

: 1374416-95-1
(R)-benzyl 3-((R)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxyethyl)pyrrolidine-1-carboxylate

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 3.16667h;
DOI:10.1021/jo3004716

Reference yield:

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

: 1374416-95-1
(R)-benzyl 3-((R)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxyethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 1374416-89-3
(S)-1-benzyl-3-((S)-2-(benzyloxy)-1-hydroxyethyl)pyrrolidin-2-one

: 1374416-95-1
(R)-benzyl 3-((R)-1-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxyethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

3.2: pH 2

3.3: pH 13

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

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

With hydrogenchloride; lithium aluminium tetrahydride; palladium on carbon; hydrogen; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; toluene;
DOI:10.1021/jo3004716