(+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide

Base Information

• Chemical Name: (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide
• CAS No.: 869468-01-9
• Molecular Formula: C₃₀H₃₈N₂O₂
• Molecular Weight: 458.644
• Mol file: 869468-01-9.mol

Synonyms:(+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide

Chemical Property of (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide

There total 4 articles about (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide 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: 55.0%

(+)-(1'S,2'S,2E)-N-(2'-tert-butyldimethylsilyloxy-1'-methylethyl-2'-phenyl)-N-methylhex-2-enamide (958637-76-8) + lithium dibenzylamide (85175-35-5) → (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide (869468-01-9) + (+)-(1'S,2'S,3S)-3-dibenzylamino-N-(2'-hydroxy-1'-methylethyl-2'-phenyl)-N-methylhexanamide (958637-77-9)

Guidance literature:

(+)-(1'S,2'S,2E)-N-(2'-tert-butyldimethylsilyloxy-1'-methylethyl-2'-phenyl)-N-methylhex-2-enamide; lithium dibenzylamide; With n-butyllithium; In hexane; toluene; at -90 ℃; for 20h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;

DOI:10.1016/j.tet.2007.08.067

Reference yield:

E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-hex-2-enamide (869468-00-8) + dibenzylamine (103-49-1) → (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide (869468-01-9) + (+)-(1'S,2'S,3S)-3-dibenzylamino-N-(2'-hydroxy-1'-methylethyl-2'-phenyl)-N-methylhexanamide (958637-77-9)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In toluene; at -90 ℃; for 7.5h;

DOI:10.1021/jo051207j

Reference yield:

(E)-2-hexenoyl chloride (97943-16-3) → (+)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide (869468-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N / tetrahydrofuran / 1.5 h / -20 °C

2: n-BuLi; TMEDA / toluene / 7.5 h / -90 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/jo051207j

upstream raw materials:

E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-hex-2-enamide

dibenzylamine

(+)-(1'S,2'S,2E)-N-(2'-tert-butyldimethylsilyloxy-1'-methylethyl-2'-phenyl)-N-methylhex-2-enamide

lithium dibenzylamide

Downstream raw materials:

(+)-(1'S,2'S,3R)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide