Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-carboxylate

Base Information

• Chemical Name: Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-carboxylate
• CAS No.: 253195-64-1
• Molecular Formula: C11H10 F3 N O6 S
• Molecular Weight: 341.265
• DSSTox Substance ID: DTXSID10442593
• Nikkaji Number: J1.252.155C
• Wikidata: Q82259953
• Mol file: 253195-64-1.mol

Synonyms:253195-64-1;Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-carboxylate;Methyl 5-oxo-6-(trifluoromethylsulfonyloxy)-2,3-dihydro-1H-indolizine-8-carboxylate;METHYL 5-OXO-6-TRIFLUOROMETHANESULFONYLOXY-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE;SCHEMBL4724230;DTXSID10442593;QBJAUKHFUPLZNQ-UHFFFAOYSA-N;DIPOTASSIUMSUCCINATETRIHYDRATE;Methyl 5-oxo-6-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,5-tetrahydroindolizine-8-carboxylate;Methyl5-oxo-6-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,5-tetrahydroindolizine-8-carboxylate;1,2,3,5-Tetrahydro-5-oxo-6-(trifluoromethylsulfonyloxy)indolizine-8-carboxylic acid methyl ester

Chemical Property of Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-carboxylate

Chemical Property:

• Melting Point: 102-103 °C
• Boiling Point: 460.2±45.0 °C(Predicted)
• PKA: -5.13±0.60(Predicted)
• PSA: 100.05000
• Density: 1 +-.0.1 g/cm3(Predicted)
• LogP: 1.89030
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 341.01809270
• Heavy Atom Count: 22
• Complexity: 686

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C2CCCN2C(=O)C(=C1)OS(=O)(=O)C(F)(F)F

Technology Process of Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-carboxylate

There total 4 articles about Methyl 5-oxo-6-[(trifluoromethanesulfonyl)oxy]-1,2,3,5-tetrahydroindolizine-8-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: 99.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (185198-42-9) → methyl 5-oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine-8-carboxylate (253195-64-1)

Guidance literature:

6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester; With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

N,N-phenylbistrifluoromethane-sulfonimide; In dichloromethane; at 20 ℃; for 6h;

Reference yield:

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 5-oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine-8-carboxylate (253195-64-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16.3333h;

DOI:10.1021/co400067q

Reference yield:

1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one (185198-40-7) → methyl 5-oxo-6-trifluoromethanesulfonyloxy-1,2,3,5-tetrahydroindolizine-8-carboxylate (253195-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh(II)

2: Et₃N

With triethylamine; rhodium⁽²⁺⁾;

DOI:10.1021/jo0511492

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester

1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one

1-(phenylsulfonylacetyl)pyrrolidin-2-one

Downstream raw materials:

6-(4-methoxy-phenylamino)-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester

6-(3,5-dimethoxy-phenylamino)-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester

6-(2-bromo-phenylamino)-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester

5-oxo-6-(2-trifluoromethyl-phenylamino)-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester