(5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine

Base Information

• Chemical Name: (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine
• CAS No.: 1268265-29-7
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.419
• Mol file: 1268265-29-7.mol

Synonyms:(5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine

Chemical Property of (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine

There total 20 articles about (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine 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: 46.0%

(5aS,8R,8aS)-5a,7,8-trimethyl-4-phenyl-2,5a,8,8a-tetrahydro-1H-cyclopenta[4,5]furo[3,2-c]pyridin-1-one (864448-19-1) + chloromethyl methyl ether (107-30-2) → (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine (1268265-29-7)

Guidance literature:

With N,N-diethyl-N-isopropylamine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ol200022a

Reference yield:

tert-butyl(((1S,2R)-2-methyl-5-(propan-2-ylidene)cyclopentyl)methoxy)diphenylsilane (876152-54-4) → (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine (1268265-29-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: ozone / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

1.3: -78 - 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.67 h / -78 °C / Inert atmosphere

2.3: 19 h / 20 °C / Inert atmosphere

3.1: pyridine; iodine / tetrachloromethane / 11.5 h / 20 °C / Inert atmosphere

4.1: copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane / 1-methyl-pyrrolidin-2-one / 6 h / 80 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

6.1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

7.1: 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

8.1: diphenylether / 0.75 h / 210 °C / Inert atmosphere

9.1: pyridine; N-iodo-succinimide / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

11.1: pyridine; Dess-Martin periodane; dimethyl sulfoxide / dichloromethane / 1 h / 20 °C / Inert atmosphere

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

13.1: zinc(II) iodide / diethyl ether; dichloromethane / 13 h / 20 °C / Inert atmosphere

14.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 24 h / 80 °C / Inert atmosphere

15.1: N,N-diethyl-N-isopropylamine / dichloromethane / 0.33 h / 20 °C

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; N-iodo-succinimide; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-azobis(isobutyronitrile); N,N-diethyl-N-isopropylamine; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) iodide; lithium hexamethyldisilazane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diphenylether; diethyl ether; hexane; dichloromethane; benzene; 4.1: Stille coupling / 11.1: Dess-Martin oxidation;

DOI:10.1021/ol200022a

Reference yield:

(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone (1268265-30-0) → (5aS,8R,8aS)-1-(methoxymethoxy)-5a,7,8-trimethyl-4-phenyl-8,8a-dihydro-5aH-cyclopenta[4,5]furo[3,2-c]pyridine (1268265-29-7)

Guidance literature:

Multi-step reaction with 12 steps

1: copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane / 1-methyl-pyrrolidin-2-one / 6 h / 80 °C / Inert atmosphere

2: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere

3: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4: 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5: diphenylether / 0.75 h / 210 °C / Inert atmosphere

6: pyridine; N-iodo-succinimide / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

8: pyridine; Dess-Martin periodane; dimethyl sulfoxide / dichloromethane / 1 h / 20 °C / Inert atmosphere

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

10: zinc(II) iodide / diethyl ether; dichloromethane / 13 h / 20 °C / Inert atmosphere

11: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 24 h / 80 °C / Inert atmosphere

12: N,N-diethyl-N-isopropylamine / dichloromethane / 0.33 h / 20 °C

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; N-iodo-succinimide; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-azobis(isobutyronitrile); N,N-diethyl-N-isopropylamine; N,N,N,N,-tetramethylethylenediamine; triphenyl-arsane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diphenylether; diethyl ether; hexane; dichloromethane; benzene; 1: Stille coupling / 8: Dess-Martin oxidation;

DOI:10.1021/ol200022a

upstream raw materials:

(2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3-methylcyclopentanone

tert-butyl(((1S,2R)-2-methyl-5-(propan-2-ylidene)cyclopentyl)methoxy)diphenylsilane

(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-4-methylcyclopent-2-enone

(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone

Refernces