(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

Base Information

Chemical Name:(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
CAS No.:207515-82-0
Molecular Formula:C₂₄H₃₀N₂O₄
Molecular Weight:410.513
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 20 articles about (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 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: 42.0%

: 207515-81-9
{(Z)-3-[(R)-8-(2-tert-Butoxycarbonylamino-ethyl)-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-6-en-6-yl]-allyl}-carbamic acid tert-butyl ester

: 207515-82-0
(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

Guidance literature:: With hydrogenchloride; water; In tetrahydrofuran;
DOI:10.1039/a709212a

Reference yield:

: 207515-62-6
(1S,4R,4aS,8aR)-7-(2-Benzyloxy-ethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

: 207515-82-0
(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

Guidance literature:: Multi-step reaction with 20 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

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; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; 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

: 207515-82-0
(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

Guidance literature:: Multi-step reaction with 16 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

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; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; tert-butyl alcohol; benzene;
DOI:10.1039/a709212a