(1'S,2R,3R)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

Base Information

• Chemical Name: (1'S,2R,3R)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine
• CAS No.: 123054-15-9
• Molecular Formula: C₁₉H₂₈N₂O₃
• Molecular Weight: 332.443
• Mol file: 123054-15-9.mol

Synonyms:

Chemical Property of (1'S,2R,3R)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2R,3R)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

There total 7 articles about (1'S,2R,3R)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine 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:

(S)-valinol (2026-48-4,473-75-6) → (1'S,2R,3R)-N2,N2,N3-tribenzyl-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-15-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / acetic acid (pH ca. 6), sodium cyanoborohydride / methanol / 16 h / Ambient temperature

2: 83 percent / neat (no solvent) / 16 h / 50 °C

3: 89 percent / diethyl ether / 1.5 h / 0 - 20 °C

4: Et₃N / tetrahydrofuran / 3 h / 0 - 20 °C

5: H₂ / 20percent Pd(OH)2/C / ethyl acetate / 48 h / 3040 Torr / Ambient temperature

6: Et₃N / CH₂Cl₂; toluene / 0.5 h / -20 °C

With hydrogen; sodium cyanoborohydride; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo00284a032

Reference yield:

N,N-dibenzyl-(R)-2-amino-3-phenylpropanal (123054-12-6) → (1'S,2R,3R)-N2,N2,N3-tribenzyl-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-15-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / neat (no solvent) / 16 h / 50 °C

2: 89 percent / diethyl ether / 1.5 h / 0 - 20 °C

3: Et₃N / tetrahydrofuran / 3 h / 0 - 20 °C

4: H₂ / 20percent Pd(OH)2/C / ethyl acetate / 48 h / 3040 Torr / Ambient temperature

5: Et₃N / CH₂Cl₂; toluene / 0.5 h / -20 °C

With hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo00284a032

Reference yield:

N-benzyl-L-valinol (42807-42-1) → (1'S,2R,3R)-N2,N2,N3-tribenzyl-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-15-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / neat (no solvent) / 16 h / 50 °C

2: 89 percent / diethyl ether / 1.5 h / 0 - 20 °C

3: Et₃N / tetrahydrofuran / 3 h / 0 - 20 °C

4: H₂ / 20percent Pd(OH)2/C / ethyl acetate / 48 h / 3040 Torr / Ambient temperature

5: Et₃N / CH₂Cl₂; toluene / 0.5 h / -20 °C

With hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jo00284a032

upstream raw materials:

phosgene

Acetic acid (S)-2-((1R,2R)-2-amino-1-ethyl-3-phenyl-propylamino)-3-methyl-butyl ester

(S)-valinol

N,N-dibenzyl-(R)-2-amino-3-phenylpropanal