N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Base Information

• Chemical Name: N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole
• CAS No.: 80516-06-9
• Molecular Formula: C₂₄H₂₇NO₅
• Molecular Weight: 409.482

Synonyms:

Chemical Property of N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole

There total 12 articles about N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole 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:

1,2-dimethoxybenzene (91-16-7) → N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole (80516-06-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 66 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 16 h / Heating

3: 89 percent / NaBH₄ / ethanol / 12 h / -20 °C

4: 76 percent / pyridine / 18 h / Ambient temperature

5: 1.) lithium isopropylcyclohexylamide, HMPA, 2.) tert-butyldimethylchlorosilane / 1.) THF, -78 deg C, 5 min, 2.) reflux, 3 h

6: 1.) SOCl₂, 2.) NH₂OH*HCl, Na₂CO₃ / 1.) benzene, DMF, reflux, 2 h, 2.) diethyl ether

7: 82.5 percent / tetrapropylammonium periodate / CHCl₃; dimethylformamide

8: 100 percent / toluene / 0.33 h / Heating

9: 78 percent / Na₂CO₃, TiCl₃ / H₂O; methanol / 18 h / Ambient temperature

10: 90 percent / NaH / tetrahydrofuran / 12 h / Ambient temperature

11: 88 percent / DME-H₂O, N-bromosuccinimide / 5 h / -18 °C

12: 90 percent / α,α'-azobis(isobutyronitrile), tributyltin hydride / benzene / 2.5 h / Heating

13: 95 percent / pyridine / 1 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; Perbenzoic acid; titanium(III) chloride; tetrapropylammonium periodate; DME-H₂O; azobisisobutyronitrile; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium hydride; sodium carbonate; lithium cyclohexylisopropylamide; tert-butyldimethylsilyl chloride; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00346a028

Reference yield:

3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one (20036-53-7) → N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole (80516-06-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / NaBH₄ / ethanol / 12 h / -20 °C

2: 76 percent / pyridine / 18 h / Ambient temperature

3: 1.) lithium isopropylcyclohexylamide, HMPA, 2.) tert-butyldimethylchlorosilane / 1.) THF, -78 deg C, 5 min, 2.) reflux, 3 h

4: 1.) SOCl₂, 2.) NH₂OH*HCl, Na₂CO₃ / 1.) benzene, DMF, reflux, 2 h, 2.) diethyl ether

5: 82.5 percent / tetrapropylammonium periodate / CHCl₃; dimethylformamide

6: 100 percent / toluene / 0.33 h / Heating

7: 78 percent / Na₂CO₃, TiCl₃ / H₂O; methanol / 18 h / Ambient temperature

8: 90 percent / NaH / tetrahydrofuran / 12 h / Ambient temperature

9: 88 percent / DME-H₂O, N-bromosuccinimide / 5 h / -18 °C

10: 90 percent / α,α'-azobis(isobutyronitrile), tributyltin hydride / benzene / 2.5 h / Heating

11: 95 percent / pyridine / 1 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; titanium(III) chloride; tetrapropylammonium periodate; DME-H₂O; azobisisobutyronitrile; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium hydride; sodium carbonate; lithium cyclohexylisopropylamide; tert-butyldimethylsilyl chloride; In tetrahydrofuran; pyridine; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00346a028

Reference yield:

4-Bromoveratrole (2859-78-1) → N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-(benzoyloxy)-2,3,3a,4,5,6,7,7a-octahydroindole (80516-06-9)

Guidance literature:

Multi-step reaction with 12 steps

2: 89 percent / NaBH₄ / ethanol / 12 h / -20 °C

3: 76 percent / pyridine / 18 h / Ambient temperature

4: 1.) lithium isopropylcyclohexylamide, HMPA, 2.) tert-butyldimethylchlorosilane / 1.) THF, -78 deg C, 5 min, 2.) reflux, 3 h

5: 1.) SOCl₂, 2.) NH₂OH*HCl, Na₂CO₃ / 1.) benzene, DMF, reflux, 2 h, 2.) diethyl ether

6: 82.5 percent / tetrapropylammonium periodate / CHCl₃; dimethylformamide

7: 100 percent / toluene / 0.33 h / Heating

8: 78 percent / Na₂CO₃, TiCl₃ / H₂O; methanol / 18 h / Ambient temperature

9: 90 percent / NaH / tetrahydrofuran / 12 h / Ambient temperature

10: 88 percent / DME-H₂O, N-bromosuccinimide / 5 h / -18 °C

11: 90 percent / α,α'-azobis(isobutyronitrile), tributyltin hydride / benzene / 2.5 h / Heating

12: 95 percent / pyridine / 1 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; thionyl chloride; titanium(III) chloride; tetrapropylammonium periodate; DME-H₂O; azobisisobutyronitrile; hydroxylamine hydrochloride; tri-n-butyl-tin hydride; sodium hydride; sodium carbonate; lithium cyclohexylisopropylamide; tert-butyldimethylsilyl chloride; In tetrahydrofuran; pyridine; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00346a028

upstream raw materials:

1,2-dimethoxybenzene

3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one

4-Bromoveratrole

3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-ol

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