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

Base Information

• Chemical Name: (2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane
• CAS No.: 617711-36-1
• Molecular Formula: C₂₀H₁₉NO
• Molecular Weight: 289.377
• Mol file: 617711-36-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane 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: 34.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal (617711-34-9) → (2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane (617711-36-1)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; at 25 ℃; for 0.5h;

2-methyl-3-(N-benzylindol-7-yl)-2(S),3(R)-epoxypropanal; In tetrahydrofuran; at 25 ℃; for 1.5h;

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

Reference yield:

7-bromo-1H-indole (51417-51-7) → (2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane (617711-36-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: KHMDS / tetrahydrofuran / 0.5 h / 25 °C

6.2: 34 percent / tetrahydrofuran / 1.5 h / 25 °C

With titanium(IV) isopropylate; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutylammomium bromide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; triethylamine; tert.-butylhydroperoxide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Heck reaction / 4.1: Sharpless asymmetric epoxidation / 6.2: Wittig reaction;

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

Reference yield:

(E)-methyl 3-(7-indolyl)-2-methacrylate (617711-17-8) → (2R,3R)-2-methyl-3-(N-benzylindol-7-yl)-2-vinyloxirane (617711-36-1)

Guidance literature:

Multi-step reaction with 5 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

5.1: KHMDS / tetrahydrofuran / 0.5 h / 25 °C

5.2: 34 percent / tetrahydrofuran / 1.5 h / 25 °C

With titanium(IV) isopropylate; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine 4-oxide monohydrate; tert.-butylhydroperoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Sharpless asymmetric epoxidation / 5.2: Wittig reaction;

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

upstream raw materials:

Methyltriphenylphosphonium bromide

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

7-bromo-1H-indole

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