(2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate
• CAS No.: 94062-52-9
• Molecular Formula: C16H21NO2^.C7H8O3S
• Molecular Weight: 431.553
• Hs Code.: 2933990090
• European Community (EC) Number: 618-998-7
• Mol file: 94062-52-9.mol

Synonyms:94062-52-9;(2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate;L-Octahydroindole-2-carboxylic acid benzyl ester 4-methylbenzenesulfonate;L-(2S,3aS,7aS)-Octahydro-1H-indole-2-carboxylic Acid Benzyl Ester Tosylate Salt;2s-(2alpha,3alpha,beta,7alpha,beta-Octahydro-1H-indole-2-carboxylic acid phenyl methyl ester;benzyl (2S,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylate;4-methylbenzenesulfonic acid;SCHEMBL1415100;PTLASYHTXGUCJU-WDTSGDEMSA-N;AMY18443;MFCD09751101;(2S,3aS,7aS)-Benzyloctahydro-1H-indole-2-carboxylate4-methylbenzenesulfonate;AKOS016010411;AS-15092;F20573;A844798;(2S,3aS,7aS)-octahydroindole-2-carboxylic acid benzyl ester para-toluene-sulphonate;(2s,3as,7as)-octahydroindole-2-carboxylic acid benzyl ester para-toluenesulfonate;(2S,3aS,7aS)-octahydroindole-2-carboxylic acid-benzyl ester para toluene sulfonate

Chemical Property of (2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate

Chemical Property:

• PSA: 101.08000
• LogP: 5.30180
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 431.17664420
• Heavy Atom Count: 30
• Complexity: 518

Purity/Quality:

99% ^*data from raw suppliers

[2S-(2α,3α,β,7α,β]-Octahydro-1H-Indole-2-CarboxylicAcidPhenylMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1CCC2C(C1)CC(N2)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1CC[C@H]2[C@@H](C1)C[C@H](N2)C(=O)OCC3=CC=CC=C3

Technology Process of (2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate

There total 2 articles about (2S,3aS,7aS)-Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate 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: 93.0%

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5,2055118-14-2) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6,185532-71-2) → (2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid phenylmethyl ester 4-methylbenzenesulfonate (94062-52-9,82717-91-7)

Guidance literature:

In toluene; for 4h; Heating;

DOI:10.1021/jm00106a030

Reference yield:

(S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → (2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid phenylmethyl ester 4-methylbenzenesulfonate (94062-52-9,82717-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / H₂ / 10percent Pd/C / acetic acid / 18 h / 50 °C / 36775.4 Torr

2: 93 percent / toluene / 4 h / Heating

With hydrogen; palladium on activated charcoal; In acetic acid; toluene;

DOI:10.1021/jm00106a030

Reference yield: 99.0%

(2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid phenylmethyl ester 4-methylbenzenesulfonate (94062-52-9,82717-91-7) + N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine (82834-12-6) → (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid benzyl ester (122454-52-8)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20 - 25 ℃;

upstream raw materials:

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

toluene-4-sulfonic acid

benzyl alcohol

(S)-indoline-2-carboxylic acid

Downstream raw materials:

(2S,3aS,7aS)-1-glycinyl>-2-<(benzyloxy)carbonyl>perhydroindole

(2S,3aS,7aS)-1-glycinyl>-2-carboxyperhydroindole

(2S,3aS,7aS)-1-glycinyl>-2-carboxyperhydroindole tert-butylamine salt

(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid benzyl ester

Refernces

• 1、 Pascard,Guilhem,Vincent,Remond,Portevin,Laubie. "Configuration and preferential solid-state conformations of perindoprilat (S-9780). Comparison with the crystal structures of other ACE inhibitors and conclusions related to structure-activity relationships". . p. 663 - 669. Retrieved 2007/10/02.