(2R)-2,3-Dihydro-1H-indole-2-ylMethanol

Base Information

• Chemical Name: (2R)-2,3-Dihydro-1H-indole-2-ylMethanol
• CAS No.: 77122-21-5
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.192
• Mol file: 77122-21-5.mol

Synonyms:

Chemical Property of (2R)-2,3-Dihydro-1H-indole-2-ylMethanol

Chemical Property:

• Melting Point: 67-68 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• Boiling Point: 309.1±11.0 °C(Predicted)
• PKA: 14.42±0.10(Predicted)
• Density: 1.120±0.06 g/cm3(Predicted)

Purity/Quality:

95-99% ^*data from raw suppliers

(2R)-2,3-Dihydro-1H-indole-2-methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2R)-2,3-Dihydro-1H-indole-2-methanol is a reagent used in the synthesis of novel hexahydropyrazino[1,2-a]indole derivatives as a potent inhibitor of apoptosis proteins antagonists with improved membrane permeability across MDR1 expressing cells.

Technology Process of (2R)-2,3-Dihydro-1H-indole-2-ylMethanol

There total 18 articles about (2R)-2,3-Dihydro-1H-indole-2-ylMethanol 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: 96.0%

aqueous THF + indoline-2-carboxylic acid methyl ester (59040-84-5,130791-93-4,141410-06-2) → 2,3-Dihydro-1H-indol-2-ylmethanol (27640-31-9,27640-33-1,77122-21-5,138969-57-0)

Guidance literature:

With sodium hydroxide; LiAlH₄; In tetrahydrofuran; diethyl ether; water;

Reference yield: 96.0%

indoline-2-carboxylic acid methyl ester (59040-84-5,130791-93-4,141410-06-2) → 2,3-Dihydro-1H-indol-2-ylmethanol (27640-31-9,27640-33-1,77122-21-5,138969-57-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3.5h; Heating;

DOI:10.1021/jm00049a015

Reference yield: 95.0%

indolin-2-yl carboxylic acid (16851-56-2,78348-24-0) → 2,3-Dihydro-1H-indol-2-ylmethanol (27640-31-9,27640-33-1,77122-21-5,138969-57-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201700977

upstream raw materials:

indoline-2-carboxylic acid methyl ester

indole-2-carboxylic acid methyl ester

indolin-2-yl carboxylic acid

methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate

Downstream raw materials:

(2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole

benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate

2-<(methoxycarbonyl)methyl>indoline

Refernces

• 1、 Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.. "Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst". supporting information. p. 5760 - 5764. Retrieved 2017/05/12.
• 2、 Clarisse, Damien,Fenet, Bernard,Fache, Fabienne. "Hexafluoroisopropanol: A powerful solvent for the hydrogenation of indole derivatives. Selective access to tetrahydroindoles or cis-fused octahydroindoles". experimental part. p. 6587 - 6594. Retrieved 2012/09/08.