(3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline

Base Information

• Chemical Name: (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline
• CAS No.: 207515-83-1
• Molecular Formula: C₁₉H₂₂N₂O₂
• Molecular Weight: 310.396

Synonyms:(3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline

Chemical Property of (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline

There total 21 articles about (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline 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:

(1S,4R,4aS,8aR)-7-(2-Benzyloxy-ethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one (207515-62-6) → (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline (207515-83-1)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) CuBr*SMe₂, Me₃SiCl, HMPA, 2.) acid / 1.) THF

2: diphenyl ether / 260 °C

3: DIBAL-H, CuI, HMPA / tetrahydrofuran

4: H₂ / 10percent Pd/C

5: imidazole / dimethylformamide

6: 70 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol

7: NaBH₄, CeCl₃*7H₂O

8: (CF₃CO₂)IPh

9: NaH / tetrahydrofuran

10: HClO₄, H₂O / tetrahydrofuran

11: 1,2-dichloro-benzene / 180 °C

12: 97 percent / I₂, pyridine / CH₂Cl₂

13: 91 percent / CuI, Et₃N / PdCl₂(PPh₃)2

14: 71 percent / TsOH / benzene

15: 100 percent / Bu₄NF / tetrahydrofuran

16: 90 percent / PPh₃, DIPAD / tetrahydrofuran

17: 86 percent / H₂ / Lindlar catalyst / methanol

18: N₂H₄*H₂O / ethanol / Heating

19: Et₃N / CH₂Cl₂

20: 42 percent / HCl, H₂O / tetrahydrofuran

21: TFA / CHCl₃

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; perchloric acid; cerium(III) chloride; copper(I) bromide dimethylsulfide complex; (CF₃CO₂)IPh; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; hydrazine hydrate; diisopropyl (E)-azodicarboxylate; triethylamine; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol; benzene;

DOI:10.1039/a709212a

Reference yield:

(R)-3-(3,4-Dimethoxy-phenyl)-3-(2-hydroxy-ethyl)-cyclohexanone → (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline (207515-83-1)

Guidance literature:

Multi-step reaction with 17 steps

1: imidazole / dimethylformamide

2: 70 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol

3: NaBH₄, CeCl₃*7H₂O

4: (CF₃CO₂)IPh

5: NaH / tetrahydrofuran

6: HClO₄, H₂O / tetrahydrofuran

7: 1,2-dichloro-benzene / 180 °C

8: 97 percent / I₂, pyridine / CH₂Cl₂

9: 91 percent / CuI, Et₃N / PdCl₂(PPh₃)2

10: 71 percent / TsOH / benzene

11: 100 percent / Bu₄NF / tetrahydrofuran

12: 90 percent / PPh₃, DIPAD / tetrahydrofuran

13: 86 percent / H₂ / Lindlar catalyst / methanol

14: N₂H₄*H₂O / ethanol / Heating

15: Et₃N / CH₂Cl₂

16: 42 percent / HCl, H₂O / tetrahydrofuran

17: TFA / CHCl₃

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; perchloric acid; cerium(III) chloride; (CF₃CO₂)IPh; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hydride; toluene-4-sulfonic acid; hydrazine hydrate; diisopropyl (E)-azodicarboxylate; triethylamine; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol; benzene;

DOI:10.1039/a709212a

Reference yield:

(R)-5-(2-Benzyloxy-ethyl)-5-(3,4-dimethoxy-phenyl)-cyclohex-2-enone (207515-64-8) → (3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline (207515-83-1)

Guidance literature:

Multi-step reaction with 19 steps

1: DIBAL-H, CuI, HMPA / tetrahydrofuran

2: H₂ / 10percent Pd/C

3: imidazole / dimethylformamide

4: 70 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol

5: NaBH₄, CeCl₃*7H₂O

6: (CF₃CO₂)IPh

7: NaH / tetrahydrofuran

8: HClO₄, H₂O / tetrahydrofuran

9: 1,2-dichloro-benzene / 180 °C

10: 97 percent / I₂, pyridine / CH₂Cl₂

11: 91 percent / CuI, Et₃N / PdCl₂(PPh₃)2

12: 71 percent / TsOH / benzene

13: 100 percent / Bu₄NF / tetrahydrofuran

14: 90 percent / PPh₃, DIPAD / tetrahydrofuran

15: 86 percent / H₂ / Lindlar catalyst / methanol

16: N₂H₄*H₂O / ethanol / Heating

17: Et₃N / CH₂Cl₂

18: 42 percent / HCl, H₂O / tetrahydrofuran

19: TFA / CHCl₃

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; perchloric acid; cerium(III) chloride; (CF₃CO₂)IPh; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; hydrazine hydrate; diisopropyl (E)-azodicarboxylate; triethylamine; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol; benzene;

DOI:10.1039/a709212a

upstream raw materials:

(3aS,9bR)-3a-(3,4-Dimethoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-pyrrolo[2,3-f]quinoline-1-carboxylic acid tert-butyl ester

(1S,4R,4aS,8aR)-7-(2-Benzyloxy-ethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

(R)-5-(2-Benzyloxy-ethyl)-5-(3,4-dimethoxy-phenyl)-cyclohex-2-enone

(1S,4R,4aS,7R,8aR)-7-(2-Benzyloxy-ethyl)-7-(3,4-dimethoxy-phenyl)-4,4a,6,7,8,8a-hexahydro-1H-1,4-methano-naphthalen-5-one

Downstream raw materials:

3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[2,3-f]quinoline

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