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

Base Information

• Chemical Name: 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
• CAS No.: 134031-41-7
• Molecular Formula: C₂₃H₃₀N₂O₂
• Molecular Weight: 366.503

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 14 articles about 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 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: 88.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (+/-)-(1R*,5S*,7S*)-4-(E)-ethylidene-7-hydroxy-7-<1-(2-(trimethylacetamido)phenyl)ethenyl>-2-azabicyclo<3.2.1>octane (134031-40-6) → N-{2-[(1R,7R,8S)-2-Eth-(E)-ylidene-11-oxo-4-aza-tricyclo[5.2.2.04,8]undec-7-yl]-phenyl}-2,2-dimethyl-propionamide (134031-41-7)

Guidance literature:

With camphor-10-sulfonic acid; sodium sulfate; In acetonitrile; at 80 ℃;

DOI:10.1021/ja00013a068

Reference yield:

cyclopent-2-enone (930-30-3) → N-{2-[(1R,7R,8S)-2-Eth-(E)-ylidene-11-oxo-4-aza-tricyclo[5.2.2.04,8]undec-7-yl]-phenyl}-2,2-dimethyl-propionamide (134031-41-7)

Guidance literature:

Multi-step reaction with 12 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

12: 88 percent / NaSO₄, camphorsulfonic acid / acetonitrile / 1 h / Heating

With tert.-butylhydroperoxide; dmap; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; chloro-trimethyl-silane; camphor-10-sulfonic acid; 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; acetonitrile;

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) → N-{2-[(1R,7R,8S)-2-Eth-(E)-ylidene-11-oxo-4-aza-tricyclo[5.2.2.04,8]undec-7-yl]-phenyl}-2,2-dimethyl-propionamide (134031-41-7)

Guidance literature:

Multi-step reaction with 3 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

3: 88 percent / NaSO₄, camphorsulfonic acid / acetonitrile / 1 h / Heating

With potassium hydroxide; camphor-10-sulfonic acid; sodium hydride; In ethanol; water; acetonitrile;

upstream raw materials:

formaldehyd

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

cyclopent-2-enone

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

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