(2S)-2-methyl-2,3-dihydro-1H-indole

Base Information

• Chemical Name: (2S)-2-methyl-2,3-dihydro-1H-indole
• CAS No.: 22160-09-4
• Molecular Formula: C9H11N
• Molecular Weight: 133.19000
• DSSTox Substance ID: DTXSID00426382
• Nikkaji Number: J723.354J
• Wikidata: Q82239311
• Mol file: 22160-09-4.mol

Synonyms:22160-09-4;(2S)-2-methyl-2,3-dihydro-1H-indole;(S)-2-methylindoline;(2S)-2,3-DIHYDRO-2-METHYL-1H-INDOLE;2beta-Methylindoline;SCHEMBL1736809;DTXSID00426382;QRWRJDVVXAXGBT-ZETCQYMHSA-N;XAA16009;MFCD19217163;VT1375;AKOS025290736;(S)-2-methyl-2,3-dihydro-1H-indole;AS-54757;CS-0053438;EN300-142517;A878678;F8881-8898

Chemical Property of (2S)-2-methyl-2,3-dihydro-1H-indole

Chemical Property:

• PSA: 12.03000
• LogP: 2.18110
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S)-2-methyl-2,3-dihydro-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC=CC=C2N1
• Isomeric SMILES: C[C@H]1CC2=CC=CC=C2N1

Technology Process of (2S)-2-methyl-2,3-dihydro-1H-indole

There total 5 articles about (2S)-2-methyl-2,3-dihydro-1H-indole 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: 28.0%

N-tosyl-L-prolyl chloride (54731-09-8,118776-39-9) + 2-methyl indoline (6872-06-6) → (R)-2-methyl-2,3-dihydro-1H-indole (22160-13-0) + (S)-(-)-2-methylindoline (22160-09-4) + N-[N'-tosyl-(2S)-propyl]-(2R)-2-methylindoline + N-[N'-tosyl-(2S)-propyl]-(2S)-2-methylindoline

Guidance literature:

In benzene; at 20 ℃; for 20h;

DOI:10.1016/S0957-4166(03)00321-5

Reference yield: 18.0%

(R)-2-phenoxypropionyl chloride (147851-69-2) + 2-methyl indoline (6872-06-6) → (2S,2'R)-2-methyl-N-(2'-phenoxypropionyl)indoline + (2R,2'R)-2-methyl-N-(2'-phenoxypropionyl)indoline + (R)-2-methyl-2,3-dihydro-1H-indole (22160-13-0) + (S)-(-)-2-methylindoline (22160-09-4)

Guidance literature:

In toluene; at 20 ℃; for 6h; Resolution of racemate;

DOI:10.1016/j.tetasy.2016.10.004

Reference yield:

2-methyl-1H-indole (95-20-5) → C9H11N + (-)-2-methyl-indoline (6872-06-6,22160-09-4,22160-13-0,138380-84-4)

Guidance literature:

With C₃₂H₁₂BF₂₄^(1-)*C₄₅H₄₆IrNO₂P⁽¹⁺⁾; hydrogen; In dichloromethane; at 20 ℃; for 24h; under 56255.6 Torr; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.200903105

upstream raw materials:

2-methyl-1H-indole

N-tosyl-L-prolyl chloride

2-methyl indoline

(R)-2-phenoxypropionyl chloride

Downstream raw materials:

N-[(2S)-2-(4-isobutylphenyl)propionyl]-(2S)-2-methylindoline

N-[(2S)-2-phenylpropionyl]-(2S)-2-methylindoline

2-{2-[(2S)-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one

Refernces

• 1、 Vakarov, Sergey A.,Gruzdev, Dmitry A.,Chulakov, Evgeny N.,Sadretdinova, Liliya Sh.,Tumashov, Andrey A.,Pervova, Marina G.,Ezhikova, Marina A.,Kodess, Mikhail I.,Levit, Galina L.,Krasnov, Victor P.,Charushin, Valery N.. "Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride". supporting information. p. 1231 - 1237. Retrieved 2016/11/23.
• 2、 Krasnov, Victor P.,Levit, Galina L.,Bukrina, Iraida M.,Andreeva, Irina N.,Sadretdinova, Liliya Sh.,Korolyova, Marina A.,Kodess, Mikhail I.,Charushin, Valery N.,Chupakhin, Oleg N.. "Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride". . p. 1985 - 1988. Retrieved 2007/10/03.