(2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 365973-26-8
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45
• Mol file: 365973-26-8.mol

Synonyms:(2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 12 articles about (2S,3aS,7aR)-7a-Allyl-octahydro-indole-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: 99.0%

benzyl chloroformate (501-53-1,94274-21-2) + (2S,3aS,7aR)-7a-Allyl-octahydro-indole-2-carboxylic acid methyl ester (365973-25-7) → (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (365973-26-8)

Guidance literature:

With potassium hydrogencarbonate; In water; ethyl acetate; for 2h;

DOI:10.1016/S0040-4020(01)00538-5

Reference yield:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3) → (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (365973-26-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: hexamethyldisilazane; n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 °C

1.2: 72 percent / hexane; tetrahydrofuran / 3.5 h

2.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

2.2: 85 percent / toluene / 0.67 h / 110 °C

3.1: 98 percent / DMAP / tetrahydrofuran / 2 h / 20 °C

4.1: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

5.1: 19 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.67 h / -78 °C

6.1: 89 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 94 percent / H₂ / Pd/C / ethanol / 30 h / 1520 Torr

8.1: 84 percent / NaHCO₃ / acetonitrile; methanol / Electrolysis

9.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

10.1: 89 percent / CF₃COOH / CH₂Cl₂ / 1 h / 20 °C

11.1: 99 percent / KHCO₃ / ethyl acetate; H₂O / 2 h

With dmap; Grubbs catalyst first generation; n-butyllithium; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; hydrogen; lithium triethylborohydride; sodium hydrogencarbonate; potassium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)00538-5

Reference yield:

(2S,4S)-2-allyl-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester (213475-89-9) → (2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (365973-26-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

1.2: 85 percent / toluene / 0.67 h / 110 °C

2.1: 98 percent / DMAP / tetrahydrofuran / 2 h / 20 °C

3.1: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

4.1: 19 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.67 h / -78 °C

5.1: 89 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 94 percent / H₂ / Pd/C / ethanol / 30 h / 1520 Torr

7.1: 84 percent / NaHCO₃ / acetonitrile; methanol / Electrolysis

8.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

9.1: 89 percent / CF₃COOH / CH₂Cl₂ / 1 h / 20 °C

10.1: 99 percent / KHCO₃ / ethyl acetate; H₂O / 2 h

With dmap; Grubbs catalyst first generation; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; hydrogen; lithium triethylborohydride; sodium hydrogencarbonate; potassium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(01)00538-5

upstream raw materials:

benzyl chloroformate

(2S,3aS,7aR)-7a-Allyl-octahydro-indole-2-carboxylic acid methyl ester

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

(2S,3aS,7aS)-1-(tert-butoxycarbonyl)octahydro-1H-indole-2-carboxylic acid

Downstream raw materials:

(2S,3aS,7aR)-7a-Allyl-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester

(2S,3aS,7aR)-7a-(2-oxoethyl)-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(2S,3aS,7aR)-7a-allyl-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester