2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester
• CAS No.: 82980-14-1
• Molecular Formula: C₂₈H₃₂N₂O₆S
• Molecular Weight: 524.638
• Mol file: 82980-14-1.mol

Synonyms:2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester

Chemical Property of 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester

There total 6 articles about 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester 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: 90.0%

dimethyl malonate sodium salt (18424-76-5) + 1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-3-ethyl-1,2,5,6-tetrahydro-pyridine-2-carbonitrile (82980-13-0) → 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester (82980-14-1)

Guidance literature:

With silver tetrafluoroborate; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1021/jo00144a009

Reference yield:

N-<β-(3-indolyl)ethyl>-3-ethylpyridinium bromide (24716-24-3) → 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester (82980-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium borohydride, 2.) tetrabutylammonium hydrogen sulfate, 50percent NaOH / 1.) MeOH, RT, 1 h, 2.) benzene, RT, 1 h

2: 96 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂; H₂O / 1 h / Ambient temperature

3: CH₂Cl₂ / 1 h / 0 °C

4: sodium acetate / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature; pH 4

5: 90 percent / silver tetrafluoroborate / tetrahydrofuran / 1.5 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; silver tetrafluoroborate; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00144a009

Reference yield:

1-Benzenesulfonyl-3-[2-(5-ethyl-1-oxy-3,6-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indole (82980-11-8) → 2-{1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-5-ethyl-1,2,3,4-tetrahydro-pyridin-4-yl}-malonic acid dimethyl ester (82980-14-1)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 1 h / 0 °C

2: sodium acetate / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature; pH 4

3: 90 percent / silver tetrafluoroborate / tetrahydrofuran / 1.5 h / Ambient temperature

With silver tetrafluoroborate; sodium acetate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00144a009

upstream raw materials:

dimethyl malonate sodium salt

1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-3-ethyl-1,2,5,6-tetrahydro-pyridine-2-carbonitrile

N-<β-(3-indolyl)ethyl>-3-ethylpyridinium bromide

1-Benzenesulfonyl-3-[2-(5-ethyl-1-oxy-3,6-dihydro-2H-pyridin-1-yl)-ethyl]-1H-indole

Downstream raw materials:

2-{(2S,3R,4S)-1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-2-cyano-3-ethyl-piperidin-4-yl}-malonic acid dimethyl ester

2-{(2S,3S,4S)-1-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethyl]-2-cyano-3-ethyl-piperidin-4-yl}-malonic acid dimethyl ester