2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol

Base Information

• Chemical Name: 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol
• CAS No.: 617711-32-7
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.365
• Mol file: 617711-32-7.mol

Synonyms:2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol

Chemical Property of 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol

There total 4 articles about 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol 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: 58.0%

(E)-3-(N-benzylindol-7-yl)-2-methyl-2-propenol (617711-30-5) → 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol (617711-32-7)

Guidance literature:

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tert.-butylhydroperoxide; In dichloromethane; toluene; at -20 ℃; for 2.5h;

DOI:10.1016/S0040-4020(03)00822-6

Reference yield:

7-bromo-1H-indole (51417-51-7) → 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol (617711-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 40 percent / Et₃N; Bu₄NBr / PdCl₂[P(o-Tol)3]2 / dimethylformamide / 2 h / 90 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 49 percent / dimethylformamide / 0 - 20 °C

3.1: 81 percent / Dibal-H / toluene / 0.5 h / -40 °C

4.1: 58 percent / diethyl L-tartrate; 4 Angstroem molecular sieves; Ti(O-i-Pr)4 / t-BuOOH / CH₂Cl₂; toluene / 2.5 h / -20 °C

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; diisobutylaluminium hydride; triethylamine; tert.-butylhydroperoxide; dichlorobis(tri-O-tolylphosphine)palladium; In dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Heck reaction / 4.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4020(03)00822-6

Reference yield:

(E)-methyl 3-(7-indolyl)-2-methacrylate (617711-17-8) → 2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol (617711-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 49 percent / dimethylformamide / 0 - 20 °C

2.1: 81 percent / Dibal-H / toluene / 0.5 h / -40 °C

3.1: 58 percent / diethyl L-tartrate; 4 Angstroem molecular sieves; Ti(O-i-Pr)4 / t-BuOOH / CH₂Cl₂; toluene / 2.5 h / -20 °C

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; tert.-butylhydroperoxide; In dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4020(03)00822-6

upstream raw materials:

(E)-3-(N-benzylindol-7-yl)-2-methyl-2-propenol

7-bromo-1H-indole

(E)-methyl 3-(7-indolyl)-2-methacrylate

(E)-methyl 3-(N-benzylindol-7-yl)-2-methacrylate

Downstream raw materials:

(2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane

2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal