(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

Base Information

Chemical Name:(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione
CAS No.:744202-09-3
Molecular Formula:C₃₀H₃₀N₂O₃
Molecular Weight:466.58
Hs Code.:

Synonyms:(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

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Chemical Property of (1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

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Technology Process of (1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

There total 4 articles about (1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione 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: 75.0%

: 5332-24-1
3-bromoquinoline

: 744202-08-2
(1R,5S,7R)-7-Ethynyl-3-(4-methoxy-benzyl)-1,5,7-trimethyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

: 744202-09-3
(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

Guidance literature:: With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 50 ℃; for 18h;
DOI:10.1039/b404311a

Reference yield:

: 109216-50-4
(1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride

: 744202-09-3
(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / LiAlH(t-BuO)3 / tetrahydrofuran / 0 °C

2.1: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 85 percent / NaI / dimethylformamide / 0 - 20 °C

4.1: K₂CO₃ / methanol / 1 h / 0 °C

4.2: 68 percent / methanol; tetrahydrofuran / 14 h / 0 - 20 °C

5.1: 75 percent / i-Pr₂NH; CuI / [Pd(PPh₃)2Cl₂] / tetrahydrofuran / 18 h / 50 °C

With copper(l) iodide; sodium hydride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; diisopropylamine; pyridinium chlorochromate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Sonogashira cross-coupling;
DOI:10.1039/b404311a

Reference yield:

: 744202-05-9
(1R,5S,7R)-7-Hydroxymethyl-1,5,7-trimethyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

: 744202-09-3
(1R,5S,7R)-3-(4-Methoxy-benzyl)-1,5,7-trimethyl-7-quinolin-3-ylethynyl-3-aza-bicyclo[3.3.1]nonane-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 85 percent / NaI / dimethylformamide / 0 - 20 °C

3.1: K₂CO₃ / methanol / 1 h / 0 °C

3.2: 68 percent / methanol; tetrahydrofuran / 14 h / 0 - 20 °C

4.1: 75 percent / i-Pr₂NH; CuI / [Pd(PPh₃)2Cl₂] / tetrahydrofuran / 18 h / 50 °C

With copper(l) iodide; sodium hydride; potassium carbonate; diisopropylamine; pyridinium chlorochromate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Sonogashira cross-coupling;
DOI:10.1039/b404311a