(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Base Information

Chemical Name:(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline
CAS No.:1438285-72-3
Molecular Formula:C₃₀H₄₄N₂OSi
Molecular Weight:476.778
Hs Code.:

Synonyms:(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

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Chemical Property of (4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

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Technology Process of (4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

There total 11 articles about (4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline 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: 34.0%

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

: 83578-59-0
3-trimethylsilyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-2-propyne

: 1438285-72-3
(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Guidance literature:: With dicarbonylcyclopentadienylcobalt; In tetrahydrofuran; at 140 ℃; for 30h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo400695c

Reference yield:

: 1225377-71-8
2-((4aR,5R,7S,8aS)-1-benzyl-8a-ethynyl-7-methyldecahydroquinolin-5-yl)acetonitrile

: 83578-59-0
3-trimethylsilyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-2-propyne

: 1438285-73-4
C₃₃H₅₂N₂OSi₂

: 1438285-72-3
(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Guidance literature:: With dicarbonylcyclopentadienylcobalt; In tetrahydrofuran; at 140 ℃; for 30h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo400695c

Reference yield:

: 89-82-7,90449-51-7
pulegone

: 1438285-72-3
(4aR,5S,10bR,12R)-1-benzyl-9-(((tert-butyldimethylsilyl)oxy)-methyl)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthroline

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium hydroxide; water / methanol / 23 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 66 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.08 h / 0 °C / Inert atmosphere

3.2: 70 h / 23 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 11 h / -78 - 23 °C / Inert atmosphere

5.1: n-butyllithium / diethyl ether; hexane / 0.68 h / -78 °C / Inert atmosphere

5.2: 0.55 h / -78 °C / Inert atmosphere

6.1: tetrahydrofuran; toluene / 0.58 h / 23 °C / Inert atmosphere

7.1: magnesium(II) perchlorate / 0.5 h / 23 °C / Inert atmosphere

8.1: copper(l) chloride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 7 h / 23 °C / Inert atmosphere

10.1: triphenylphosphine; 1H-imidazole / tetrachloromethane / 15 h / 77 °C / Inert atmosphere

11.1: dicarbonylcyclopentadienylcobalt / tetrahydrofuran / 30 h / 140 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; magnesium(II) perchlorate; dicarbonylcyclopentadienylcobalt; water; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; lithium hydroxide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jo400695c