(3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Base Information

• Chemical Name: (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
• CAS No.: 108431-24-9
• Molecular Formula: C₂₀H₁₉N₃O₃
• Molecular Weight: 349.389
• Mol file: 108431-24-9.mol

Synonyms:

Chemical Property of (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

There total 8 articles about (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione 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:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione (108431-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / NaOH; Bu₄NHSO₄ / CH₂Cl₂

2: 93 percent / PPTS; Na₂SO₄ / CH₂Cl₂

3: 100 percent / mCPBA; K₂CO₃ / CH₂Cl₂ / 0 - 25 °C

4: 97 percent / TFA / CH₂Cl₂ / 0.08 h

5: 88 percent / H₂ / Pd/C / methanol

6: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

7: H₂ / Pd/C / methanol

With sodium hydroxide; afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; potassium carbonate; sodium sulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b308288a

Reference yield:

(2S,3aR,8aR)-3a-Hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester (643751-49-9) → (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione (108431-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

2: H₂ / Pd/C / methanol

With afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b308288a

Reference yield:

3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (643751-48-8) → (3S,5aS,10bR,11aS)-3-Benzyl-10b-hydroxy-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione (108431-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / H₂ / Pd/C / methanol

2: O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; afluorophosphate; NEt₃ / dimethylformamide

3: H₂ / Pd/C / methanol

With afluorophosphate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetr; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b308288a

upstream raw materials:

cyclo(L-tryptophyl-L-phenylalanyl)

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

(2S,3aR,8aR)-3a-Hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

3a-hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester