(S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide
• CAS No.: 1443007-97-3
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.45
• Mol file: 1443007-97-3.mol

Synonyms:(S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide

Chemical Property of (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide

There total 16 articles about (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide 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: 79.0%

(R)-2-((E)-(2,2-dimethylpropylidene)amino)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide (1443007-93-9) + trifluoromethanesulfonic acid 3-bromo-propyl ester (103935-48-4) → (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide (1443007-97-3)

Guidance literature:

(R)-2-((E)-(2,2-dimethylpropylidene)amino)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃; for 0.25h; Inert atmosphere;

trifluoromethanesulfonic acid 3-bromo-propyl ester; In tetrahydrofuran; at -50 ℃; for 1.5h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 23 ℃; for 2h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol401337p

Reference yield:

tert-butyl ((S)-1-(((1S,2S)-2-hydroxy-1,2-diphenylethyl)(methyl)amino)-1-oxopropan-2-yl)carbamate (1443008-04-5) → (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide (1443007-97-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.62 h / 0 - 23 °C / Inert atmosphere

2.1: benzene / 0.5 h / 23 °C / 200 Torr / Inert atmosphere

3.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

3.2: 3.5 h / -50 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 3 h / 23 °C / Inert atmosphere

5.1: water / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere

7.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2.12 h / 0 - 23 °C / Inert atmosphere

8.1: dichloromethane; benzene / 0.83 h / 23 °C / Molecular sieve; Inert atmosphere

9.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

9.2: 1.5 h / -50 °C / Inert atmosphere

9.3: 2 h / 23 °C / Inert atmosphere

With hydrogenchloride; water; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; benzene;

DOI:10.1021/ol401337p

Reference yield:

(S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide (1443008-06-7) → (S)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpyrrolidine-2-carboxamide (1443007-97-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: benzene / 0.5 h / 23 °C / 200 Torr / Inert atmosphere

2.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

2.2: 3.5 h / -50 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 3 h / 23 °C / Inert atmosphere

4.1: water / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere

6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2.12 h / 0 - 23 °C / Inert atmosphere

7.1: dichloromethane; benzene / 0.83 h / 23 °C / Molecular sieve; Inert atmosphere

8.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C / Inert atmosphere

8.2: 1.5 h / -50 °C / Inert atmosphere

8.3: 2 h / 23 °C / Inert atmosphere

With hydrogenchloride; water; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; benzene;

DOI:10.1021/ol401337p

upstream raw materials:

tert-butyl ((S)-1-(((1S,2S)-2-hydroxy-1,2-diphenylethyl)(methyl)amino)-1-oxopropan-2-yl)carbamate

(R)-2-((E)-(2,2-dimethylpropylidene)amino)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide

trifluoromethanesulfonic acid 3-bromo-propyl ester

(S)-2-((E)-(2,2-dimethylpropylidene)amino)-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N-methylpropanamide

Refernces