(R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide

Base Information

• Chemical Name: (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide
• CAS No.: 1380325-41-6
• Molecular Formula: C₂₇H₃₁NO₂
• Molecular Weight: 401.549
• Mol file: 1380325-41-6.mol

Synonyms:(R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide

Chemical Property of (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide

There total 14 articles about (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide 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: 85.0%

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide (1380325-35-8) + benzyl bromide (100-39-0) → (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide (1380325-41-6)

Guidance literature:

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide; With n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 3h; Inert atmosphere;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; hexane; at -40 ℃; for 0.25h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; hexane; at -40 ℃; for 1.25h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/anie.201200370

Reference yield: 71.0%

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide (1380325-31-4) + ethyl iodide (75-03-6) → (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide (1380325-41-6) + (S)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide (1380325-56-3)

Guidance literature:

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide; With n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 3h; Inert atmosphere;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h; Inert atmosphere;

ethyl iodide; In tetrahydrofuran; hexane; at 0 ℃; for 18.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/anie.201200370

Reference yield:

N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]formamide (39664-88-5) → (R)-2-benzyl-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide (1380325-41-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 0.67 h / 0 - 23 °C / Inert atmosphere

1.2: 2 h / 120 °C / Cooling with ice; Inert atmosphere

2.1: tetrahydrofuran; diethyl ether / 2.5 h / -40 - 23 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 22.17 h / 0 - 23 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.75 h / 0 - 23 °C / Inert atmosphere

5.1: pyridine; n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C / Inert atmosphere

5.2: 0.92 h / 0 °C / Inert atmosphere

6.1: n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 3 h / -78 - 0 °C / Inert atmosphere

6.2: 0.25 h / -40 °C / Inert atmosphere

6.3: 1.25 h / -40 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1002/anie.201200370

upstream raw materials:

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-3-phenylpropanamide

ethyl iodide

(R)-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethylbutanamide

benzyl bromide

Downstream raw materials:

CF₃O₃S^(1-)*C₂₇H₃₀NO⁽¹⁺⁾