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

Base Information

Chemical Name:(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
CAS No.:219557-47-8
Molecular Formula:C₂₄H₂₄N₂O₃
Molecular Weight:388.466
Hs Code.:

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

There total 17 articles about (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-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: 81.0%

: 219557-83-2
(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

: 219557-47-8
(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: With perchloric acid; In water;
DOI:10.1021/jo9813989

Reference yield: 62.0%

: 219558-11-9
(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

: 219557-47-8
(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: With potassium osmate(VI); potassium metaperiodate; In water; at 0 ℃; for 4h;
DOI:10.1021/jo9813989

Reference yield:

: 100-52-7
benzaldehyde

: 219557-47-8
(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Guidance literature:: Multi-step reaction with 11 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

9: DIPEA, trifluoroacetic anhydride / CH₂Cl₂ / 0.67 h / Ambient temperature

10: KBH₄ / ethanol / 4 h / 75 °C

11: 62 percent / K₂OsO₄*2H₂O, KIO₄ / H₂O / 4 h / 0 °C

With sodium tetrahydroborate; potassium osmate(VI); potassium borohydride; potassium metaperiodate; trimethylsilyl trifluoromethanesulfonate; ammonia; water; magnesium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; benzoic acid; trifluoroacetic anhydride; lithium chloride; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo9813989