(7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate

Base Information

• Chemical Name: (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate
• CAS No.: 1428243-88-2
• Molecular Formula: C₂₇H₃₉N₃O₆S
• Molecular Weight: 533.689

Synonyms:

Chemical Property of (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate

There total 9 articles about (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate 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:

(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-1-hydroxy-3-methyldec-6-en-5-one (1428243-80-4) → (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate (1428243-88-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: toluene / 12.5 h / 20 °C / Inert atmosphere; Reflux

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

4.1: 20% palladium hydroxide-activated charcoal; hydrogen; water / ethyl acetate / 12 h / 20 °C

5.1: toluene / 1 h / 20 °C / Inert atmosphere

6.1: N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride / toluene / 3 h / 20 °C / Inert atmosphere

6.2: 3 h / Inert atmosphere; Reflux

7.1: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere

8.1: tris-(trimethylsilyl)silane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile / toluene / 12 h / 50 °C / Inert atmosphere

8.2: 3 h / 20 °C / Inert atmosphere

9.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

10.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere

With dmap; tetrapropylammonium perruthennate; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride; tris-(trimethylsilyl)silane; 20% palladium hydroxide-activated charcoal; water; hydrogen; tetra-(n-butyl)ammonium iodide; caesium carbonate; 4-methylmorpholine N-oxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.201206863

Reference yield:

(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-methyl-5-oxodec-6-enal (1428243-81-5) → (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate (1428243-88-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: toluene / 12.5 h / 20 °C / Inert atmosphere; Reflux

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

3.1: 20% palladium hydroxide-activated charcoal; hydrogen; water / ethyl acetate / 12 h / 20 °C

4.1: toluene / 1 h / 20 °C / Inert atmosphere

5.1: N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride / toluene / 3 h / 20 °C / Inert atmosphere

5.2: 3 h / Inert atmosphere; Reflux

6.1: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere

7.1: tris-(trimethylsilyl)silane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile / toluene / 12 h / 50 °C / Inert atmosphere

7.2: 3 h / 20 °C / Inert atmosphere

8.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

9.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere

With dmap; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride; tris-(trimethylsilyl)silane; 20% palladium hydroxide-activated charcoal; water; hydrogen; tetra-(n-butyl)ammonium iodide; caesium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.201206863

Reference yield:

(5aR,7aS,8S,8aS,11S,12aS,13aS)-8,8a-bis(3-((tert-butyldimethylsilyl)oxy)propyl)-11-methyl-5,5a,8,8a,10,11,12,12a-octahydroindeno[1',2':5,6][1,4]oxazino[4,3-a]indole-7,9(7aH,13aH)-dione (1428243-83-7) → (7aS,8R,9aS,11R,13S,13aS)-tert-butyl 11-methyl-4-((4-nitrophenyl)sulfonyl)tetradecahydro-1H-8,13-epiminoindeno[1,7a-e]azonine-14-carboxylate (1428243-88-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: 20% palladium hydroxide-activated charcoal; hydrogen; water / ethyl acetate / 12 h / 20 °C

3.1: toluene / 1 h / 20 °C / Inert atmosphere

4.1: N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride / toluene / 3 h / 20 °C / Inert atmosphere

4.2: 3 h / Inert atmosphere; Reflux

5.1: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere

6.1: tris-(trimethylsilyl)silane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile / toluene / 12 h / 50 °C / Inert atmosphere

6.2: 3 h / 20 °C / Inert atmosphere

7.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere

With dmap; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; N,N,N,N,-tetramethylethylenediamine; monochloromethanesulfonyl chloride; tris-(trimethylsilyl)silane; 20% palladium hydroxide-activated charcoal; water; hydrogen; tetra-(n-butyl)ammonium iodide; caesium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.201206863

upstream raw materials:

(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-1-hydroxy-3-methyldec-6-en-5-one

(S,E)-10-(tert-butyldimethylsilyloxy)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-methyl-5-oxodec-6-enal

(5aR,7aS,8S,8aS,11S,12aS,13aS)-8,8a-bis(3-((tert-butyldimethylsilyl)oxy)propyl)-11-methyl-5,5a,8,8a,10,11,12,12a-octahydroindeno[1',2':5,6][1,4]oxazino[4,3-a]indole-7,9(7aH,13aH)-dione

2,2,3,3,14,14,15,15-octamethyl-4,13-dioxa-3,14-disilahexadec-8-yne

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