(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

Base Information

Chemical Name:(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester
CAS No.:185394-36-9
Molecular Formula:C₁₈H₁₉NO₅
Molecular Weight:329.353
Hs Code.:

Synonyms:(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

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Chemical Property of (2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

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Technology Process of (2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

There total 3 articles about (2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester 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: 74.0%

: 185394-35-8
(2S-(2β,3aβ,6α,7aβ))-2,3,3a,6,7,7a-hexahydro-6-acetyloxy-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

: 185394-36-9
(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

Guidance literature:: With palladium diacetate; triethylamine; triphenylphosphine; In toluene; for 2h; Heating;
DOI:10.1016/0040-4020(96)00871-X

Reference yield:

: 144534-49-6
(2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 185394-36-9
(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / CeCl₃, NaBH₄ / methanol / 0.17 h

2: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

3: 74 percent / Pd(OAc)2, Ph₃P, Et₃N / toluene / 2 h / Heating

With dmap; palladium diacetate; sodium tetrahydroborate; cerium(III) chloride; triethylamine; triphenylphosphine; In methanol; dichloromethane; toluene;
DOI:10.1016/0040-4020(96)00871-X

Reference yield:

: 185394-34-7
(2S,3aR,6S,7aR)-1-benzyl 2-methyl 3a,6-dihydroxy-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate

: 185394-36-9
(2S-(2β,3aβ,7aβ))-2,3,3a,7a-tetrahydro-3a-hydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 74 percent / Pd(OAc)2, Ph₃P, Et₃N / toluene / 2 h / Heating

With dmap; palladium diacetate; triethylamine; triphenylphosphine; In dichloromethane; toluene;
DOI:10.1016/0040-4020(96)00871-X