(1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol

Base Information

• Chemical Name: (1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol
• CAS No.: 1352317-55-5
• Molecular Formula: C₁₈H₂₂BrNOS₂
• Molecular Weight: 412.415
• Mol file: 1352317-55-5.mol

Synonyms:(1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol

Chemical Property of (1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol

There total 1 articles about (1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol 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: 87.0%

3-bromo-2-picoline (38749-79-0) + (7aS)-5,5-(ethylenedithio)-7a-methyl-1,2,3,5,6,7,7a-heptahydro-1-indenone (248257-39-8) → (1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol (1352317-55-5)

Guidance literature:

3-bromo-2-picoline; With lithium diisopropyl amide; In diethyl ether; hexane; at -20 ℃; for 2h; Inert atmosphere;

(7aS)-5,5-(ethylenedithio)-7a-methyl-1,2,3,5,6,7,7a-heptahydro-1-indenone; In diethyl ether; hexane; at -20 ℃; for 1h; Inert atmosphere;

With water; In diethyl ether; hexane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.028

Reference yield:

(1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol (1352317-55-5) → (1'R,7a'S)-7a'-methyl-5'-phenyl-2',6',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-indene] (1352317-69-1)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 80 °C / Inert atmosphere

2: water; bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; dichloromethane / 0.17 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 1 h / -20 - 0 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water; toluene / 3 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; palladium diacetate; sodium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: Buchwald-Hartwig cyclization / 4: Suzuki coupling;

DOI:10.1016/j.tet.2011.10.028

Reference yield:

(1'R,7a'S)-1'-((3-bromopyridin-2-yl)methyl)-7a'-methyl-1',2',3',6',7',7a'-hexahydrospiro[[1,3]dithiolane-2,5'-inden]-1'-ol (1352317-55-5) → 4-((1'R,7a'S)-7a'-methyl-2',6',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-inden]-5'-yl)phenol (1352317-72-6)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 3 h / 80 °C / Inert atmosphere

2: water; bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; dichloromethane / 0.17 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 1 h / -20 - 0 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; water; toluene / 3 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; palladium diacetate; sodium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: Buchwald-Hartwig cyclization / 4: Suzuki coupling;

DOI:10.1016/j.tet.2011.10.028

upstream raw materials:

3-bromo-2-picoline

(7aS)-5,5-(ethylenedithio)-7a-methyl-1,2,3,5,6,7,7a-heptahydro-1-indenone

Downstream raw materials:

(1'R,7a'S)-7a'-methyl-5'-phenyl-2',6',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-indene]

4-((1'R,7a'S)-7a'-methyl-2',6',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-inden]-5'-yl)phenol