(+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane

Base Information

• Chemical Name: (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane
• CAS No.: 134031-40-6
• Molecular Formula: C₂₂H₃₀N₂O₂
• Molecular Weight: 354.492
• Mol file: 134031-40-6.mol

Synonyms:(+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane

Chemical Property of (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane

There total 13 articles about (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane 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: 90.0%

N-(2-{1-[(1R,5S,7S)-4-Eth-(E)-ylidene-7-hydroxy-2-(2,2,2-trifluoro-acetyl)-2-aza-bicyclo[3.2.1]oct-7-yl]-vinyl}-phenyl)-2,2-dimethyl-propionamide (147806-04-0) → (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane (134031-40-6)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 3h; Heating;

Reference yield:

cyclopent-2-enone (930-30-3) → (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane (134031-40-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) t-BuLi, 2.) 2-thienylCuCNLi, 3.) Me₃SiCl

2: 91 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

3: 1.) 1,1,3,3-tetramethyl-1,3-diphenyl-disilazane, n-BuLi, 3.) Pd(PPh₃)4

4: 1.) MeLi, 2.) t-BuLi

5: t-BuOOH, Triton B / tetrahydrofuran / 2 h / -23 °C

6: 56 percent / tetrahydrofuran / 3 h / Ambient temperature

7: 97 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

8: diisopropylethylamine / CH₂Cl₂ / 0.75 h

9: LiCl / dimethylformamide / 2 h / Ambient temperature

10: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, from 50 deg C to 60 deg C, 3 h

11: 90 percent / KOH / ethanol; H₂O / 3 h / Heating

With tert.-butylhydroperoxide; dmap; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; chloro-trimethyl-silane; 1,1,3,3-tetramethyl-1,3-diphenyldisilazane; tetrabutyl ammonium fluoride; methyllithium; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydride; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(+/-)-(1R*,2R*,4R*)-4-<1-(chloromethyl)-1-(E)-propenyl>-1-<1-(2-(trimethylacetamido)phenyl)ethenyl>-6-oxabicyclo<3.1.0>hexane (134031-42-8) → (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane (134031-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, from 50 deg C to 60 deg C, 3 h

2: 90 percent / KOH / ethanol; H₂O / 3 h / Heating

With potassium hydroxide; sodium hydride; In ethanol; water;

upstream raw materials:

N-(2-{1-[(1R,5S,7S)-4-Eth-(E)-ylidene-7-hydroxy-2-(2,2,2-trifluoro-acetyl)-2-aza-bicyclo[3.2.1]oct-7-yl]-vinyl}-phenyl)-2,2-dimethyl-propionamide

cyclopent-2-enone

(E)-3-<1-(hydroxymethyl)-1-propenyl>cyclopentanone

(E)-3-<1-(((triisopropylsilyl)oxy)methyl)-1-propenyl>cyclopentanone

Downstream raw materials:

N-{2-[(1R,7R,8S)-2-Eth-(E)-ylidene-11-oxo-4-aza-tricyclo[5.2.2.0^4,8]undec-7-yl]-phenyl}-2,2-dimethyl-propionamide