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

Base Information

Chemical Name:(-)-methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
CAS No.:219557-95-6
Molecular Formula:C₂₇H₂₉N₃O₃
Molecular Weight:443.546
Hs Code.:

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

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

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

There total 10 articles about (-)-methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 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: 87.0%

: 219557-89-8
(-)-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

: 219557-95-6
(-)-methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: With ammonia; In methanol; for 120h; Ambient temperature;
DOI:10.1021/jo9813989

Reference yield:

: 100-52-7
benzaldehyde

: 219557-95-6
(-)-methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: Multi-step reaction with 8 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

7: 84 percent / PhCO₂H, hydroquinone / benzene / 10 h / Heating

8: 87 percent / NH₃ / methanol / 120 h / Ambient temperature

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; ammonia; water; magnesium sulfate; triethylamine; hydroquinone; benzoic acid; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9813989

Reference yield:

: 7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8
(S)-tryptophan methyl ester hydrochloride

: 219557-95-6
(-)-methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: Multi-step reaction with 7 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

6: 84 percent / PhCO₂H, hydroquinone / benzene / 10 h / Heating

7: 87 percent / NH₃ / methanol / 120 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; ammonia; water; triethylamine; hydroquinone; benzoic acid; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9813989