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

Base Information

• Chemical Name: 2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal
• CAS No.: 617711-34-9
• Molecular Formula: C₁₉H₁₇NO₂
• Molecular Weight: 291.349
• Mol file: 617711-34-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal 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: 27.0%

2-methyl-3-(N-benzylindol-7-yl)-2(R),3(R)-epoxypropanol (617711-32-7) → 2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal (617711-34-9)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine 4-oxide monohydrate; In dichloromethane; at 20 ℃;

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(S),3(R)-epoxypropanal (617711-34-9)

Guidance literature:

Multi-step reaction with 5 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

5.1: 27 percent / TPAP; 4-methylmorpholine N-oxide monohydrate; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; 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(S),3(R)-epoxypropanal (617711-34-9)

Guidance literature:

Multi-step reaction with 4 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

4.1: 27 percent / TPAP; 4-methylmorpholine N-oxide monohydrate; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With titanium(IV) isopropylate; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; 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:

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

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