N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

Base Information

Chemical Name:N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide
CAS No.:1619983-40-2
Molecular Formula:C₂₈H₃₆N₂O₄
Molecular Weight:464.605
Hs Code.:

Synonyms:N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

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Chemical Property of N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

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Technology Process of N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

There total 13 articles about N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide 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: 70.0%

: 1619984-26-7
N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dimethoxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

: 1619983-40-2
N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

Guidance literature:: N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dimethoxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide; With boron tribromide; In dichloromethane; at 20 ℃; Inert atmosphere; Reflux;

With hydrogenchloride; In water; isopropyl alcohol; at 85 ℃; for 0.75h;

Reference yield:

: 1619983-08-2
[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](3,5-dimethoxyphenyl)methanone

: 1619983-40-2
N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: borane-THF / tetrahydrofuran / 1.67 h / 0 - 20 °C / Inert atmosphere

1.2: 1.33 h / 0 - 65 °C

2.1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C

3.1: sodium hydroxide / tetrahydrofuran; methanol / 3.5 h / 80 °C

4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.2: 2 h

5.1: borane-THF / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

5.2: 2 h / 20 °C / Cooling with ice

6.1: pyridine / 1.5 h / Cooling with ice; Inert atmosphere

7.1: sodium azide / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

8.1: water; triphenylphosphine / tetrahydrofuran / 25 h / 20 °C / Reflux

9.1: dicyclohexyl-carbodiimide / dichloromethane / 22 h / 20 °C / Inert atmosphere

10.1: boron tribromide / dichloromethane / 20 °C / Inert atmosphere; Reflux

10.2: 0.75 h / 85 °C

With pyridine; sodium azide; borane-THF; potassium tert-butylate; water; boron tribromide; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: |Wittig Olefination;

Reference yield:

: 1619983-07-1
(1R,2R,4aS,8aS)-1-[(3,5-dimethoxyphenyl)carbonyl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

: 1619983-40-2
N-{[(2S,3R,4S,4aS,8aS)-4-[(3,5-dihydroxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]methyl}pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: tin(IV) chloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 1.67 h / 0 - 20 °C / Inert atmosphere

2.2: 1.33 h / 0 - 65 °C

3.1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C

4.1: sodium hydroxide / tetrahydrofuran; methanol / 3.5 h / 80 °C

5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.2: 2 h

6.1: borane-THF / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

6.2: 2 h / 20 °C / Cooling with ice

7.1: pyridine / 1.5 h / Cooling with ice; Inert atmosphere

8.1: sodium azide / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

9.1: water; triphenylphosphine / tetrahydrofuran / 25 h / 20 °C / Reflux

10.1: dicyclohexyl-carbodiimide / dichloromethane / 22 h / 20 °C / Inert atmosphere

11.1: boron tribromide / dichloromethane / 20 °C / Inert atmosphere; Reflux

11.2: 0.75 h / 85 °C

With pyridine; sodium azide; borane-THF; potassium tert-butylate; water; boron tribromide; tin(IV) chloride; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: |Wittig Olefination;