(2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate
• CAS No.: 110714-44-8
• Molecular Formula: C₂₇H₂₉N₃O₉S
• Molecular Weight: 571.608
• Mol file: 110714-44-8.mol

Synonyms:

Chemical Property of (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate

There total 5 articles about (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate 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: 93.2%

(R)-N-tosylproline (110771-95-4) + ethyl 2-bromo-2-(6′-cyano-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate (110714-43-7) → (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate (110714-44-8,126639-36-9,126639-37-0)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

Reference yield:

ethyl 2-(6′-cyan-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate (58610-65-4) → (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate (110714-44-8,126639-36-9,126639-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) 60percent sodium hydride, 2) bromine / 1) DME, room temperature, 0.5 h, 2) room temperature, 1 h

2: 93.2 percent / Na₂CO₃ / dimethylformamide / 1 h / 70 °C

With bromine; sodium hydride; sodium carbonate; In N,N-dimethyl-formamide;

Reference yield:

6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine (58610-63-2) → (2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate (110714-44-8,126639-36-9,126639-37-0)

Guidance literature:

Multi-step reaction with 4 steps

1: chloro-trimethyl-silane / dichloromethane / 72 h / 25 °C / Inert atmosphere

2: sodium hydroxide / toluene; ethanol / 3 h / 100 °C

3: bromine; sodium hydroxide / 0.5 h / 30 °C

4: sodium carbonate / N,N-dimethyl-formamide / 100 °C

With chloro-trimethyl-silane; bromine; sodium carbonate; sodium hydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(R)-N-tosylproline

ethyl 2-bromo-2-(6′-cyano-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate

ethyl 2-(6′-cyan-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate

methyl 6-cyano-1-hydroxy-7-methyl-5-oxo-3,5-dihydroindolizine-2-carboxylate

Downstream raw materials:

(R)-((S)-2-(6′-cyano-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate

ethyl (R)-2--2-<6-cyano-1,1-(ethylenedioxy)-5-oxo-1,2,3,5-tetrahydroindolizin-7-yl>butanoate

camptothecin

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione