(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

Base Information

Chemical Name:(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol
CAS No.:96502-76-0
Molecular Formula:C₂₂H₂₅NO₄
Molecular Weight:367.445
Hs Code.:

Synonyms:(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

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Technology Process of (9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

There total 13 articles about (9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol 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: 96.0%

: 96502-75-9
(+/-)-(9R^*,9aS^*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole

: 96502-76-0
(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

Guidance literature:: With potassium carbonate; In methanol; for 2h; Ambient temperature;
DOI:10.1021/ja00299a022

Reference yield:

: 2568-24-3
2-phenyl-4,7-dihydro-1,3-dioxepine

: 96502-76-0
(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

Guidance literature:: Multi-step reaction with 12 steps

1: LiAlH₄, AlCl₃ / diethyl ether / 1.) 0 deg C to RT, 30 min; 2.) 2 h

2: pyridinium chlorochromate, Celite / CH₂Cl₂ / 3 h

3: trimethyl borate, Zn / tetrahydrofuran / 6 h

4: LiAlH₄ / diethyl ether / 0.25 h

5: 80 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 16 h / Ambient temperature

7: 1.) Hg(OAc)2, 90 percent HNO₃; 2.) conc. HCl, Zn / 1.) Ac₂O, glacial AcOH, 0 deg C, 5 min; 2.) methanol, 25 deg C, 15 min

8: CBr₄, triphenylphosphine / CH₂Cl₂; diethyl ether / 0.5 h / 25 °C

9: 2.) 0.5 N aq. NaOH / 1.) CH₂Cl₂, 40 min; 2.) ether

10: 85 percent MCPBA / CH₂Cl₂

11: diisopropylamine / CCl₄ / 0.17 h / Heating

12: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; Trimethyl borate; carbon tetrabromide; Celite; mercury(II) diacetate; nitric acid; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane;
DOI:10.1021/ja00299a022

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 96502-76-0
(9S,9aR)-9-Benzyloxymethyl-5,7-dimethoxy-6-methyl-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-ol

Guidance literature:: Multi-step reaction with 10 steps

1: trimethyl borate, Zn / tetrahydrofuran / 6 h

2: LiAlH₄ / diethyl ether / 0.25 h

3: 80 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 16 h / Ambient temperature

5: 1.) Hg(OAc)2, 90 percent HNO₃; 2.) conc. HCl, Zn / 1.) Ac₂O, glacial AcOH, 0 deg C, 5 min; 2.) methanol, 25 deg C, 15 min

6: CBr₄, triphenylphosphine / CH₂Cl₂; diethyl ether / 0.5 h / 25 °C

7: 2.) 0.5 N aq. NaOH / 1.) CH₂Cl₂, 40 min; 2.) ether

8: 85 percent MCPBA / CH₂Cl₂

9: diisopropylamine / CCl₄ / 0.17 h / Heating

10: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; Trimethyl borate; carbon tetrabromide; mercury(II) diacetate; nitric acid; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane;
DOI:10.1021/ja00299a022