(3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
CAS No.:217796-98-0
Molecular Formula:C₂₉H₃₀N₆O₄
Molecular Weight:526.595
Hs Code.:

(3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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 (3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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 (3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

There total 6 articles about (3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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: 81.0%

: 217796-97-9
(S)-2-{[(2S,3aR,8aR)-3a-(1,1-Dimethyl-allyl)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carbonyl]-amino}-3-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-propionic acid methyl ester

: 217796-98-0
(3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-2,3,6,10b,11,11a-hexahydro-5aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione

Guidance literature:: With methanol; ammonium hydroxide; for 72h; Ambient temperature;
DOI:10.1016/S0040-4039(98)01957-1

Reference yield:

: 3958-60-9
2-nitrophenylmethyl bromide

: 217796-98-0
(3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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 5 steps

1: 70 percent / benzene / Heating

2: TFA / CH₂Cl₂

3: 77 percent / DCC, HOBt, DIEA / CH₂Cl₂

4: 76 percent / TMSI / 1 h / 0 °C

5: 81 percent / 10percent NH₄OH/MeOH / 72 h / Ambient temperature

With methanol; ammonium hydroxide; trimethylsilyl iodide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; benzene;
DOI:10.1016/S0040-4039(98)01957-1

Reference yield:

: 217796-94-6
(S)-2-Amino-3-[1-(2-nitro-benzyl)-1H-imidazol-4-yl]-propionic acid methyl ester

: 217796-98-0
(3S,5aS,10bR,11aS)-10b-(1,1-Dimethyl-allyl)-3-[1-(2-nitro-benzyl)-1H-imidazol-4-ylmethyl]-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 3 steps

1: 77 percent / DCC, HOBt, DIEA / CH₂Cl₂

2: 76 percent / TMSI / 1 h / 0 °C

3: 81 percent / 10percent NH₄OH/MeOH / 72 h / Ambient temperature

With methanol; ammonium hydroxide; trimethylsilyl iodide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1016/S0040-4039(98)01957-1