5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

Base Information

Chemical Name:5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole
CAS No.:277317-35-8
Molecular Formula:C₂₈H₃₃ClN₂O₅
Molecular Weight:513.033
Hs Code.:

Synonyms:5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

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Chemical Property of 5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

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Technology Process of 5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

There total 7 articles about 5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]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: 100.0%

: 277317-31-4
7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester

: 277317-35-8
5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 1h;
DOI:10.1021/jo000297j

Reference yield:

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

: 277317-35-8
5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / DMAP / CH₂Cl₂ / 0.5 h / 25 °C

2: 98 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

3: 100 percent / NaH / dimethylformamide / 1 h / 25 °C

4: 100 percent / Bu₃SnH; AIBN / toluene / 1 h / 90 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Acylation / 2: amide cleavage / 3: Alkylation / 4: Cyclization;
DOI:10.1021/jo000297j

Reference yield:

: 124417-92-1
N⁵,1-Dibenzoyl-5-amino-7-benzyloxyindole

: 277317-35-8
5-(benzyloxy)-1-(chloromethyl)-3,6-bis(tert-butyloxycarbonyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole

Guidance literature:: Multi-step reaction with 6 steps

1: 45 percent / N-iodosuccinimide; TsOH / tetrahydrofuran / 40 h / 25 °C

2: 99 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

3: 93 percent / DMAP / CH₂Cl₂ / 0.5 h / 25 °C

4: 98 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

5: 100 percent / NaH / dimethylformamide / 1 h / 25 °C

6: 100 percent / Bu₃SnH; AIBN / toluene / 1 h / 90 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Iodination / 2: amide cleavage / 3: Acylation / 4: amide cleavage / 5: Alkylation / 6: Cyclization;
DOI:10.1021/jo000297j