(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-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:(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
CAS No.:191155-41-6
Molecular Formula:C₂₅H₂₄N₆O₃
Molecular Weight:456.504
Hs Code.:

Synonyms:(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

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

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

There total 9 articles about (5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-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: 96.0%

: o-azidobenzoic anhydride

: 191155-40-5
(5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

: 191155-41-6
(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ja991558d

Reference yield:

: 96238-68-5
tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate

: 191155-41-6
(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / PPTS / CH₂Cl₂

2: 57 percent / MeOTf; 2,6-di-(tert-butyl)pyridine / CH₂Cl₂

3: aq. NaOH / methanol; tetrahydrofuran / Heating

4: 93 percent / cyanuric fluoride; pyridine / CH₂Cl₂ / -15 °C

5: NaHCO₃ / H₂O; CH₂Cl₂

6: NH₃; DMAP / methanol

7: 96 percent / KHMDS / tetrahydrofuran / -78 °C

With pyridine; dmap; sodium hydroxide; trifluoro-[1,3,5]triazine; 2,6-di-tert-butyl-pyridine; ammonia; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydrogencarbonate; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; water; 1: Condensation / 2: prenylation / 3: Hydrolysis / 4: Substitution / 5: Condensation / 6: Cyclization / 7: Acylation;
DOI:10.1021/ja991558d

Reference yield:

: 159333-19-4
(2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid 1,8-di-tert-butyl ester

: 191155-41-6
(5aS,10bR,11aS)-2-(2-Azido-benzoyl)-10b-(1,1-dimethyl-allyl)-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / cyanuric fluoride; pyridine / CH₂Cl₂ / -15 °C

2: NaHCO₃ / H₂O; CH₂Cl₂

3: NH₃; DMAP / methanol

4: 96 percent / KHMDS / tetrahydrofuran / -78 °C

With pyridine; dmap; trifluoro-[1,3,5]triazine; ammonia; potassium hexamethylsilazane; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; 1: Substitution / 2: Condensation / 3: Cyclization / 4: Acylation;
DOI:10.1021/ja991558d