(S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 189265-59-6
• Molecular Formula: C₃₃H₄₄N₂O₄
• Molecular Weight: 532.723
• Mol file: 189265-59-6.mol

Synonyms:

Chemical Property of (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 2 articles about (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 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: 72.0%

tryptamine (61-54-1) + (+)-(1'R,3'R,4'S)-8'-Phenyl-p-menthan-3'-yl(4S)-2-oxo-3,4,5,6-tetrahydro-2H-pyran-4-ylacetate (189265-58-5) → (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (189265-59-6)

Guidance literature:

In toluene; at 110 ℃; for 7.5h;

DOI:10.1039/a700834a

Reference yield:

(E)-5-(2-Bromo-1-ethoxy-ethoxy)-pent-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (189265-57-4) → (S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (189265-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₃SnH, AIBN / benzene / 3.5 h / Heating

2: 72 percent / toluene / 7.5 h / 110 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; benzene;

DOI:10.1039/a700834a

Reference yield:

(S)-5-Hydroxy-3-{[2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-pentanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (189265-59-6) → (R)-(2,3,4,6,7,12-Hexahydro-indolo[2,3-a]quinolizin-2-yl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (1027944-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeSO₂Cl, Et₃N, 2.) KH, 18-crown-6 / 1.) benzene, 20 deg C, 1 h, 2.) MeOCH₂CH₂OMe, 20 deg C, 1.5 h

2: POCl₃ / acetonitrile / 1.5 h / Heating

With 18-crown-6 ether; potassium hydride; methanesulfonyl chloride; triethylamine; trichlorophosphate; In acetonitrile;

DOI:10.1039/a700834a

upstream raw materials:

tryptamine

(+)-(1'R,3'R,4'S)-8'-Phenyl-p-menthan-3'-yl(4S)-2-oxo-3,4,5,6-tetrahydro-2H-pyran-4-ylacetate

(E)-5-(2-Bromo-1-ethoxy-ethoxy)-pent-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Downstream raw materials:

(-)-(4S)-4-((1R,3R,4S)-8-phenylmenthyloxycarbonylmethyl)-N-[2-(indol-3-yl)ethyl]piperidin-2-one

(R)-(2,3,4,6,7,12-Hexahydro-indolo[2,3-a]quinolizin-2-yl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester