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

Base Information

• Chemical Name: (+/-)-(9R^*,9aS^*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole
• CAS No.: 96502-75-9
• Molecular Formula: C₂₄H₂₇NO₅
• Molecular Weight: 409.482

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (+/-)-(9R^*,9aS^*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole 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:

C30H33NO6Se (96502-74-8) → (+/-)-(9R*,9aS*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole (96502-75-9)

Guidance literature:

With diisopropylamine; In tetrachloromethane; for 0.166667h; Yield given; Heating;

DOI:10.1021/ja00299a022

Reference yield:

2-phenyl-4,7-dihydro-1,3-dioxepine (2568-24-3) → (+/-)-(9R*,9aS*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole (96502-75-9)

Guidance literature:

Multi-step reaction with 11 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

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

DOI:10.1021/ja00299a022

Reference yield:

4-benzyloxycrotonaldehyde (69152-87-0) → (+/-)-(9R*,9aS*)-8-acetoxy-9-<(benzyloxy)methyl>-9,9-dihydro-5,7-dimethoxy-6-methyl-3H-pyrrolo<1,2-a>indole (96502-75-9)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1021/ja00299a022

upstream raw materials:

C₃₀H₃₃NO₆Se

2-phenyl-4,7-dihydro-1,3-dioxepine

4-benzyloxycrotonaldehyde

(Z)-4-benzyloxy-but-2-en-1-ol

Downstream raw materials:

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

Acetic acid (9S,9aR)-9-benzyloxymethyl-5,7-dimethoxy-6-methyl-4-oxy-9,9a-dihydro-3H-pyrrolo[1,2-a]indol-8-yl ester

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

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