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

Base Information

• Chemical Name: 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
• CAS No.: 1352317-72-6
• Molecular Formula: C₂₂H₂₁NO₂
• Molecular Weight: 331.414
• Mol file: 1352317-72-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 56.0%

(1'R,7a'S)-7a'-methyl-2',6',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-inden]-5'-yl trifluoromethanesulfonate (1352317-65-7) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 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:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In tetrahydrofuran; water; toluene; for 3h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.10.028

Reference yield:

3-bromo-2-picoline (38749-79-0) → 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 5 steps

1.1: lithium diisopropyl amide / diethyl ether; hexane / 2 h / -20 °C / Inert atmosphere

1.2: 1 h / -20 °C / Inert atmosphere

1.3: 20 °C / Inert atmosphere

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

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

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

5.1: 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; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; 2.1: Buchwald-Hartwig cyclization / 5.1: Suzuki coupling;

DOI:10.1016/j.tet.2011.10.028

Reference yield:

(1'R,7a'S)-7a'-methyl-2',3',7',7a'-tetrahydro-3H-spiro[furo[3,2-b]pyridine-2,1'-inden]-5'(6'H)-one (1352317-62-4) → 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 2 steps

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

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 2: Suzuki coupling;

DOI:10.1016/j.tet.2011.10.028

upstream raw materials:

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

(p-hydroxyphenyl)boronic acid

(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

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