methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Base Information

Chemical Name:methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate
CAS No.:280573-03-7
Molecular Formula:C₂₆H₂₈N₂O₆
Molecular Weight:464.518
Hs Code.:

Synonyms:methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

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Chemical Property of methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

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Technology Process of methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

There total 12 articles about methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate 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: 60.0%

: 280573-01-5
methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-[[(2',2',6',6'-tetramethylpiperidino)oxy]methyl]-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

: 280573-03-7
methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Guidance literature:: With acetic acid; zinc; In tetrahydrofuran; water; at 60 ℃; for 11h;
DOI:10.1021/jo000177b

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 280573-03-7
methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / Et₃N / dioxane / 24 h / 70 °C

2: 78 percent / Pd(PPh₃)4; n-Bu₃N / 12 h / 100 °C

3: 91 percent / methanol / 1.5 h / 4 - 25 °C

4: 88 percent / N-iodosuccinimide; TsOH / tetrahydrofuran; methanol / 46.5 h / 4 - 25 °C

5: 94 percent / NaH / dimethylformamide / 2.5 h / 25 °C

6: 54 percent / Bu₃SnH / benzene / 3.5 h / 70 °C

7: 60 percent / Zn; AcOH / tetrahydrofuran; H₂O / 11 h / 60 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyl-amine; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; benzene; 1: Acylation / 2: Carboxylation / 3: Substitution / 4: Iodination / 5: Alkylation / 6: Dehalogenation / 7: Reduction;
DOI:10.1021/jo000177b

Reference yield:

: 100-39-0
benzyl bromide

: 280573-03-7
methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / NaH; KI / dimethylformamide / 24 h / 25 °C

2: SnCl₂*2H₂O / ethyl acetate / 0.5 h / 70 °C

3: 74 percent / Et₃N / dioxane / 24 h / 70 °C

4: 78 percent / Pd(PPh₃)4; n-Bu₃N / 12 h / 100 °C

5: 91 percent / methanol / 1.5 h / 4 - 25 °C

6: 88 percent / N-iodosuccinimide; TsOH / tetrahydrofuran; methanol / 46.5 h / 4 - 25 °C

7: 94 percent / NaH / dimethylformamide / 2.5 h / 25 °C

8: 54 percent / Bu₃SnH / benzene / 3.5 h / 70 °C

9: 60 percent / Zn; AcOH / tetrahydrofuran; H₂O / 11 h / 60 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyl-amine; tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; potassium iodide; tin(ll) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Alkylation / 2: Reduction / 3: Acylation / 4: Carboxylation / 5: Substitution / 6: Iodination / 7: Alkylation / 8: Dehalogenation / 9: Reduction;
DOI:10.1021/jo000177b