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

Base Information

Chemical Name:(2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate
CAS No.:1421232-65-6
Molecular Formula:C₁₈H₂₁NO₅
Molecular Weight:331.368
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

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Technology Process of (2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

There total 3 articles about (2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-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: 55.0%

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

: 1421232-65-6
(2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

Guidance literature:: With hydrazine hydrate; acetic acid; In dichloromethane; at 0 - 20 ℃; for 11h;
DOI:10.1002/anie.201207307

Reference yield:

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

: 1421232-65-6
(2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.75 h / 20 °C

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

2.2: 0.25 h / 0 °C

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

With dihydrogen peroxide; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; 3.1: |Wharton Fragmentation;
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

: 1421232-65-6
(2S,3aR,4R,7aR)-1-benzyl 2-methyl 4-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 2 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

With dihydrogen peroxide; hydrazine hydrate; acetic acid; In methanol; dichloromethane; water; 2.1: |Wharton Fragmentation;
DOI:10.1002/anie.201207307