(-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide

Base Information

• Chemical Name: (-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide
• CAS No.: 1262432-89-2
• Molecular Formula: C₂₇H₃₈N₂O₅
• Molecular Weight: 470.609
• Mol file: 1262432-89-2.mol

Synonyms:(-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide

Chemical Property of (-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide

There total 1 articles about (-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide 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: 90.0%

(R,R)-(-)-pseudoephedrine acetamide (52305-20-1) + (R)-tert-butyl methyl(1-oxo-3-phenylpropan-2-yl)carbamate (181646-92-4) → (-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide (1262432-89-2)

Guidance literature:

(R,R)-(-)-pseudoephedrine acetamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h;

(R)-tert-butyl methyl(1-oxo-3-phenylpropan-2-yl)carbamate; In tetrahydrofuran; at -100 ℃; for 7.33333h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %de; diastereoselective reaction;

DOI:10.1021/jo101878j

Reference yield:

(-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide (1262432-89-2) → (3R,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-5-phenylpentanoic acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; sodium hydroxide / 1,4-dioxane; methanol / 2 h / Reflux

1.2: pH 3

2.1: tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere

2.2: 0.75 h / 0 °C / Inert atmosphere

3.1: dipyridine chromium trioxide / dichloromethane / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere

With sodium tetrahydroborate; water; dipyridine chromium trioxide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo101878j

Reference yield:

(-)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-N-methyl-N-((R,R)-2-phenyl-2-hydroxy-1-methylethyl)-5-phenylpentanamide (1262432-89-2) → (-)-(4S,5R)-5-benzyl-4-hydroxy-1-methylpyrrolidin-2-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; sodium hydroxide / 1,4-dioxane; methanol / 2 h / Reflux

1.2: pH 3

2.1: tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere

2.2: 0.75 h / 0 °C / Inert atmosphere

3.1: dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: potassium carbonate / water / 0.5 h / Reflux; Inert atmosphere

With water; potassium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo101878j

upstream raw materials:

(R,R)-(-)-pseudoephedrine acetamide

(R)-tert-butyl methyl(1-oxo-3-phenylpropan-2-yl)carbamate

Downstream raw materials:

(+)-(3S,4R)-4-(tert-butoxycarbonyl(methyl)amino)-3-hydroxy-5-phenylpentanoic acid methyl ester