Methyl 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Base Information

• Chemical Name: Methyl 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate
• CAS No.: 185198-42-9
• Molecular Formula: C10H11 N O4
• Molecular Weight: 209.202
• DSSTox Substance ID: DTXSID40442748
• Nikkaji Number: J1.252.154E
• Wikidata: Q82260206
• Mol file: 185198-42-9.mol

Synonyms:185198-42-9;METHYL 6-HYDROXY-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE;Methyl 6-hydroxy-5-oxo-2,3-dihydro-1H-indolizine-8-carboxylate;METHYL6-HYDROXY-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE;DTXSID40442748;DBQRNYRACVXZRS-UHFFFAOYSA-N;E87615;5-Oxo-6-hydroxy-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester;6-Hydroxy-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid methyl ester

Chemical Property of Methyl 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Chemical Property:

• PSA: 68.53000
• LogP: 0.28670
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 209.06880783
• Heavy Atom Count: 15
• Complexity: 394

Purity/Quality:

97% ^*data from raw suppliers

METHYL-6-HYDROXY-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

There total 4 articles about Methyl 6-hydroxy-5-oxo-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: 86.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one (185198-40-7) → 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (185198-42-9)

Guidance literature:

With dirhodium tetraacetate;

DOI:10.1021/jo961690l

Reference yield: 70.0%

1-(p-tosyldiazoacetyl)pyrrolidin-2-one (939411-19-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (185198-42-9)

Guidance literature:

dirhodium tetraacetate; In benzene; for 2h; Heating / reflux;

Reference yield:

1-(phenylsulfonylacetyl)pyrrolidin-2-one (907969-47-5) → 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (185198-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N; p-acetamidophenylsulfonyl azide / acetonitrile / 0 - 20 °C

2: 86 percent / Rh(OAc)2 / benzene / 14 h / Heating

With rhodium(II) acetate; 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; benzene; 1: Substitution / 2: Cycloaddition;

DOI:10.1021/jo9911600

upstream raw materials:

acrylic acid methyl ester

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

1-(phenylsulfonylacetyl)pyrrolidin-2-one

1-(p-tosyldiazoacetyl)pyrrolidin-2-one

Downstream raw materials:

indolizidine

methyl-5-oxo-6-phenyl-1,2,3-trihydroindolizine-8-carboxylic acid

5-oxo-6-(2-trifluoromethyl-phenylamino)-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