(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:701261-86-1
Molecular Formula:C₁₈H₂₂BrNO₄
Molecular Weight:396.281
Hs Code.:

Synonyms:(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of (2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 3 articles about (2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 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: 89.0%

: 701262-24-0
(2S,4S)-5-Acetoxy-4-but-3-enyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 701261-86-1
(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: With stannic bromide; In dichloromethane; at -78 ℃; Inert atmosphere;
DOI:10.1021/ol901702k

Reference yield:

: 701261-82-7
methyl (2S,4S)-4-but-3-enyl-5-oxo-pyrrolidine-2-carboxylate

: 701261-86-1
(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 1 h

2.1: LiHBEt₃ / tetrahydrofuran / 1 h / -78 °C

2.2: Et₃N; DMAP / CH₂Cl₂

3.1: 61 percent / SnBr₄ / CH₂Cl₂ / 0.17 h / -78 °C

With stannic bromide; lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja030669g

Reference yield:

: 701261-70-3
(2S,4S)-2-but-3-enyl-4-tert-butoxycarbonylaminopentanedioic acid dimethyl ester

: 701261-86-1
(2S,3aS,6S,7aS)-6-bromo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: HCO₂H / 5 h / 20 °C

1.2: toluene / 1.5 h / Heating

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 82 percent / tetrahydrofuran / 1 h

3.1: LiHBEt₃ / tetrahydrofuran / 1 h / -78 °C

3.2: Et₃N; DMAP / CH₂Cl₂

4.1: 61 percent / SnBr₄ / CH₂Cl₂ / 0.17 h / -78 °C

With formic acid; stannic bromide; lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja030669g