methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

Base Information

• Chemical Name: methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate
• CAS No.: 736138-02-6
• Molecular Formula: C₃₀H₃₅ClN₂O₇
• Molecular Weight: 571.07
• Mol file: 736138-02-6.mol

Synonyms:methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

Chemical Property of methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate

There total 20 articles about methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-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: 33.1%

1-(1,1-dimethylethyl)-2-methyl 5-[(3-chloro-2-propenyl)-(1,1-dimethylethoxy)carbonylamino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate (919535-10-7) → methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (736138-02-6) + methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1R)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (736138-18-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 4h;

Reference yield:

3-(benzyloxy)-5-nitrobenzaldehyde (881422-32-8) → methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (736138-02-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C

2: 68 percent / xylene / 7 h / 140 °C

3: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C

4: 98 percent / Zn; NH₄Cl / acetone; H₂O / 0.5 h / 25 °C

5: 227 mg / tetrahydrofuran / 10 h / 25 °C

6: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C

7: 86 percent / NaH / dimethylformamide / 2 h / 0 °C

8: Bu₃SnH; AIBN / benzene / 1 h / 80 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; sodium hydride; ammonium chloride; acetic acid; zinc; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone; toluene; xylene; benzene;

DOI:10.1021/ja064228j

Reference yield:

methyl 2-azido-3-(3-benzyloxy-5-nitrophenyl)acrylate → methyl 5-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-(1S)-(chloromethyl)-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate (736138-02-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 68 percent / xylene / 7 h / 140 °C

2: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C

3: 98 percent / Zn; NH₄Cl / acetone; H₂O / 0.5 h / 25 °C

4: 227 mg / tetrahydrofuran / 10 h / 25 °C

5: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C

6: 86 percent / NaH / dimethylformamide / 2 h / 0 °C

7: Bu₃SnH; AIBN / benzene / 1 h / 80 °C

With dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; ammonium chloride; acetic acid; zinc; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; toluene; xylene; benzene;

DOI:10.1021/ja064228j

upstream raw materials:

1-(1,1-dimethylethyl)-2-methyl 5-[(3-chloro-2-propenyl)-(1,1-dimethylethoxy)carbonylamino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate

3-(benzyloxy)-5-nitrobenzaldehyde

1-(1,1-dimethylethyl)-2-methyl 5-[[(1,1-dimethylethoxy)-carbonyl]amino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate

di-tert-butyl dicarbonate