2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole

Base Information

• Chemical Name: 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole
• CAS No.: 219557-56-9
• Molecular Formula: C₂₂H₂₄N₂O₄
• Molecular Weight: 380.444

Synonyms:2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole

Chemical Property of 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole

There total 8 articles about 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole 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: 97.0%

2-<(methoxycarbonyl)methyl>-3-<2(S)-(methoxycarbonyl)-2-b-(tert-butoxycarbonyl)-Nb-benzylamino>ethyl>indole (219558-95-9) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(Nb-benzylamino)ethyl>indole (219557-56-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo9813989

Reference yield:

benzaldehyde (100-52-7) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(Nb-benzylamino)ethyl>indole (219557-56-9)

Guidance literature:

Multi-step reaction with 6 steps

1: MgSO₄ / CH₂Cl₂ / 5 h

2: NaBH₄ / methanol / 1 h / 0 °C

3: 28.5 g / Et₃N / CH₂Cl₂ / Ambient temperature

5: 33.1 g / LiCl, H₂O / dimethylformamide / 4 h / 135 °C

6: 97 percent / TMSOTf, Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; water; magnesium sulfate; triethylamine; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9813989

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(Nb-benzylamino)ethyl>indole (219557-56-9)

Guidance literature:

Multi-step reaction with 5 steps

2: 28.5 g / Et₃N / CH₂Cl₂ / Ambient temperature

4: 33.1 g / LiCl, H₂O / dimethylformamide / 4 h / 135 °C

5: 97 percent / TMSOTf, Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; water; triethylamine; lithium chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9813989

upstream raw materials:

2-<(methoxycarbonyl)methyl>-3-<2(S)-(methoxycarbonyl)-2-b-(tert-butoxycarbonyl)-N^b-benzylamino>ethyl>indole

(S)-tryptophan methyl ester hydrochloride

methyl N-benzyl-L-tryptophanate

N_b-benzylidene-L-tryptophan methyl ester

Downstream raw materials:

(-)-methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

(-)-methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

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