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

Base Information

Chemical Name: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
CAS No.:96502-86-2
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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: 99.7%

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

: 96502-86-2
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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/ja00299a022

Reference yield:

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

: 96502-86-2
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

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: 99.7 percent / 85 percent MCPBA / CH₂Cl₂ / 0.5 h / Ambient temperature

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:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 96502-86-2
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

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: 99.7 percent / 85 percent MCPBA / CH₂Cl₂ / 0.5 h / Ambient temperature

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