(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

Base Information

Chemical Name:(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate
CAS No.:1421232-64-5
Molecular Formula:C₁₈H₁₉NO₅
Molecular Weight:329.353
Hs Code.:

Synonyms:(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

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Chemical Property of (2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

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Technology Process of (2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

There total 1 articles about (2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate 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: 100.0%

: 320748-59-2
(2S,7aR)-6-oxo-2,3,5,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 1421232-64-5
(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1002/anie.201207307

Reference yield: 97.0%

: 1421232-64-5
(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

: 1421232-51-0
(1aS,3aR,5S,6aR,6bS)-4-benzyl 5-methyl 2-oxohexahydro-1aH-oxireno[2,3-e]indole-4,5(2H)-dicarboxylate

Guidance literature:: (2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate; With dihydrogen peroxide; In methanol; water; at 0 ℃; for 0.0833333h;

With sodium hydroxide; In methanol; water; at 0 ℃; for 0.25h;
DOI:10.1002/anie.201207307

Reference yield:

: 1421232-64-5
(2S,3aS,7aR)-1-benzyl 2-methyl 6-oxo-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

: 1421232-54-3
(2S,3aR,7R,7aS)-1-benzyl 2-methyl 7-hydroxy-4-oxo-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dihydrogen peroxide / methanol; water / 0.08 h / 0 °C

1.2: 0.25 h / 0 °C

2.1: hydrazine hydrate; acetic acid / dichloromethane / 11 h / 0 - 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

5.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 0.5 h / -78 °C

6.1: silica gel / dichloromethane

With dihydrogen peroxide; 3,3-dimethyldioxirane; silica gel; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetone; 2.1: |Wharton Fragmentation / 3.1: |Dess-Martin Oxidation / 6.1: |Wharton Fragmentation;
DOI:10.1002/anie.201207307