tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate

Base Information

• Chemical Name: tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate
• CAS No.: 1393359-48-2
• Molecular Formula: C₂₄H₃₇NO₄
• Molecular Weight: 403.562
• Mol file: 1393359-48-2.mol

Synonyms:tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate

Chemical Property of tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate

There total 1 articles about tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate 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: 59.0%

lithium (R)-N-methyl-N-(R-methyl-p-methoxybenzyl)-amide + acrolein (107-02-8,25068-14-8) + tert-butyl (E)-hepta-2,6-dienoate (270901-71-8) → tert-butyl (2S,3R)-2-[(1R)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate (1393359-49-3) + tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate (1393359-48-2)

Guidance literature:

lithium (R)-N-methyl-N-(R-methyl-p-methoxybenzyl)-amide; tert-butyl (E)-hepta-2,6-dienoate; In tetrahydrofuran; hexanes; at -78 ℃; for 2h; Inert atmosphere;

acrolein; In tetrahydrofuran; hexanes; at -78 - 20 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol3020607

Reference yield: 95.0%

tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate (1393359-48-2) → tert-butyl (1S,2S,7R)-2-hydroxy-7-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}cyclohept-3-ene-1-carboxylate (1393359-52-8)

Guidance literature:

tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate; With Grubbs catalyst first generation; In dichloromethane; at 30 ℃; for 12h; Inert atmosphere;

With tris(hydroxymethyl)phosphine; silica gel; triethylamine; In dichloromethane; at 20 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol3020607

Reference yield:

tert-butyl (2S,3R)-2-[(1S)-1-hydroxyprop-2-en-1-yl]-3-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}hept-6-enoate (1393359-48-2) → Pseudococaine hydrochloride (53-21-4,6363-57-1,21030-50-2,56222-58-3,78993-15-4,109496-04-0,109582-53-8,112547-19-0,113775-05-6,131829-34-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Grubbs catalyst first generation / dichloromethane / 12 h / 30 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); iodine / dichloromethane / 12 h / 20 °C / Inert atmosphere

2.2: 0.25 h / 20 °C / Inert atmosphere

2.3: 5 h / Inert atmosphere; Reflux

3.1: thionyl chloride / 5 h / 50 °C / Inert atmosphere

3.2: 4 h / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: hydrogenchloride / methanol / 0.08 h / 20 °C / Inert atmosphere

With Grubbs catalyst first generation; hydrogenchloride; dmap; thionyl chloride; 2,2'-azobis(isobutyronitrile); iodine; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ol3020607

upstream raw materials:

acrolein

tert-butyl (E)-hepta-2,6-dienoate

Downstream raw materials:

tert-butyl (1S,2S,7R)-2-hydroxy-7-{[(1R)-1-(4-methoxyphenyl)ethyl](methyl)amino}cyclohept-3-ene-1-carboxylate

tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydroiodide

α-methyl-p-methoxybenzyl ethyl ether

methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride

Refernces