tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate

Base Information

• Chemical Name: tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate
• CAS No.: 136019-53-9
• Molecular Formula: C₃₂H₃₅N₃O₄
• Molecular Weight: 525.648
• Mol file: 136019-53-9.mol

Synonyms:tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate

Chemical Property of tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate

There total 11 articles about tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate 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: 78.5%

methyl-(+/-)-β-<<(2-phenylethyl)amino>carbonyl>-β-<<(tricyclo<3.3.1.1>dec-2-yloxy)carbonyl>amino>-1H-indole-3-butanoate (134557-58-7) → tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate (136019-53-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)86480-2

Reference yield:

2-adamantyl chloroformate (53120-53-9) → tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate (136019-53-9)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 12 h / Ambient temperature

2: 88 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 2327.2 Torr

3: dicyclohexylcarbodiamide / tetrahydrofuran / 2 h

4: tetrahydrofuran

5: 78.5 percent / 0.01 M LiOH / tetrahydrofuran / 1 h / 0 °C

With lithium hydroxide; hydrogen; 1,3-Dicyclohexylurea; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4020(01)86480-2

Reference yield:

(+/-)-benzyl-N-formyltryptophan (134558-09-1) → tricyclo<3.3.1.1>dec-2-yl-(+/-)-<3-(1H-indol-3-ylmethyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidinyl>carbamate (136019-53-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 68 percent / 4-dimethylaminopyridine / dimethylformamide / 24 h / Ambient temperature

2: 87 percent / Et₃N, triphosgene / CH₂Cl₂ / 10 h / Ambient temperature

3: 1.) hexamethylphosphourous amide, lithium bistrimethylsilylamide / 1.) THF, -78 deg C, 30 min 2.) a) -78 deg C, 3 h b) rt, 1 h

4: ethanolic HCl, H₂O / ethanol / 4 h / Ambient temperature

5: Et₃N / tetrahydrofuran / 12 h / Ambient temperature

6: 88 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 2327.2 Torr

7: dicyclohexylcarbodiamide / tetrahydrofuran / 2 h

8: tetrahydrofuran

9: 78.5 percent / 0.01 M LiOH / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; bis(trichloromethyl) carbonate; water; hydrogen; 1,3-Dicyclohexylurea; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86480-2

upstream raw materials:

methyl-(+/-)-β-<<(2-phenylethyl)amino>carbonyl>-β-<<(tricyclo<3.3.1.1>dec-2-yloxy)carbonyl>amino>-1H-indole-3-butanoate

2-adamantyl chloroformate

(+/-)-benzyl-N-formyltryptophan

Methyl-(+/-)-β-amino-β[(phenylmethoxy)carbonyl]-1H-indole-3-butanoate