8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

Base Information

• Chemical Name: 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]
• CAS No.: 247061-45-6
• Molecular Formula: C₃₆H₃₈N₄
• Molecular Weight: 526.725
• Mol file: 247061-45-6.mol

Synonyms:8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

Chemical Property of 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

There total 14 articles about 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] 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:

2-iodophenylamine (615-43-0) → 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] (247061-45-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 92 percent / Me₃Al / toluene / 20 °C

2: 87 percent / NaH / dimethylformamide

3: 70 percent / BCl₃ / -78 °C

4: 80 percent / camphorsulfonic acid monohydrate

5: 90 percent / (Ph₃P)2PdCl₂; Et₃N / N,N-dimethyl-acetamide / 100 °C

6: camphorsulfonic acid monohydrate / tetrahydrofuran

7: NaBH₄ / methanol

8: Pb(OAc)4 / benzene

9: NaBH₄ / methanol

10: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating

11: (PhO)2P(O)N₃; Ph₃P; diethyl azodicarboxylate / tetrahydrofuran

12: 100 percent / H₂ / 10 percent Pd/C / ethanol

13: methanol / 110 °C

14: NaBH(OAc)3 / methanol

With lead(IV) acetate; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; diphenyl phosphoryl azide; camphor-10-sulfonic acid; hydrogen; trimethylaluminum; boron trichloride; sodium tris(acetoxy)borohydride; sodium hydride; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; benzene; 1: Condensation / 2: N-benzylation / 3: debenzylation / 4: Condensation / 5: Cyclization / 6: Hydrolysis / 7: Reduction / 8: Ring cleavage / 9: Reduction / 10: Reduction / 11: azidation; Mitsunobu reaction / 12: Reduction / 13: Rearrangement / 14: reductive methylation;

DOI:10.1021/ja991714g

Reference yield:

2,2'-((3S,3'S)-1,1'-dibenzyl-2,2'-dioxo-[3,3'-biindoline]-3,3'-diyl)diacetaldehyde (371252-55-0) → 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] (247061-45-6)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / methanol

2: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / Heating

3: (PhO)2P(O)N₃; Ph₃P; diethyl azodicarboxylate / tetrahydrofuran

4: 100 percent / H₂ / 10 percent Pd/C / ethanol

5: methanol / 110 °C

6: NaBH(OAc)3 / methanol

With sodium tetrahydroborate; diphenyl phosphoryl azide; hydrogen; sodium tris(acetoxy)borohydride; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 1: Reduction / 2: Reduction / 3: azidation; Mitsunobu reaction / 4: Reduction / 5: Rearrangement / 6: reductive methylation;

DOI:10.1021/ja991714g

Reference yield:

C34H34N2O3 (247061-41-2) → 8,8'-dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] (247061-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1: (PhO)2P(O)N₃; Ph₃P; diethyl azodicarboxylate / tetrahydrofuran

2: 100 percent / H₂ / 10 percent Pd/C / ethanol

3: methanol / 110 °C

4: NaBH(OAc)3 / methanol

With diphenyl phosphoryl azide; hydrogen; sodium tris(acetoxy)borohydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; 1: azidation; Mitsunobu reaction / 2: Reduction / 3: Rearrangement / 4: reductive methylation;

DOI:10.1021/ja991714g

upstream raw materials:

formaldehyd

8,8'-dibenzyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]

2-iodophenylamine

2,2'-((3S,3'S)-1,1'-dibenzyl-2,2'-dioxo-[3,3'-biindoline]-3,3'-diyl)diacetaldehyde

Downstream raw materials:

Calycanthin

Refernces