(2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

Base Information

• Chemical Name: (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid
• CAS No.: 1415684-17-1
• Molecular Formula: C₂₄H₂₅NO₄
• Molecular Weight: 391.467
• Mol file: 1415684-17-1.mol

Synonyms:(2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

Chemical Property of (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

There total 7 articles about (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid 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: 65.0%

(2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-3-nitromethyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline (1415684-16-0) → (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid (1415684-17-1)

Guidance literature:

With acetic acid; sodium nitrite; In N,N-dimethyl-formamide; at 50 ℃; for 7h;

DOI:10.1016/j.tet.2012.10.038

Reference yield:

C24H28N2O5 → (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid (1415684-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 20 °C / Reflux

2: sodium nitrite; acetic acid / N,N-dimethyl-formamide / 7 h / 50 °C

With acetic acid; trifluoroacetic acid; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.10.038

Reference yield:

2-[4-(benzyloxy)phenyl]ethylamine hydrochloride (2982-54-9) → (2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline-3-carboxylic acid (1415684-17-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / water; diethyl ether

2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

3: trifluoroacetic acid / dichloromethane / 9.5 h / 20 °C

4: sodium nitrite; acetic acid / N,N-dimethyl-formamide / 4 h / 50 °C

With benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium hydroxide; sodium nitrite; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(2S,3R,3aS,12bR)-1,2,3,3a,4,5,7,8-octahydro-11-benzyloxy-2-methyl-3-nitromethyl-5-oxo-cyclopenta[2,3]pyrrolo[2,1-a]isoquinoline

tyrosamine

2-[4-(benzyloxy)phenyl]ethylamine hydrochloride

N-(tert-butoxycarbonyl)-2-[4-(benzyloxy)phenyl]ethylamine