(S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate

Base Information

• Chemical Name: (S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate
• CAS No.: 1339021-76-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Mol file: 1339021-76-9.mol

Synonyms:

Chemical Property of (S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate

There total 1 articles about (S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-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:

methyl 4-hydroxy-4-(2-methyl-1-tosylpyrrolidin-2-yl)but-2-ynoate → (S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate (1339021-76-9) + 3-nitrophenyl 4-methylbenzenesulfonate (3899-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

2: C₁₈H₃₃AuP⁽¹⁺⁾*BF₄^(1-) / 1,2-dichloro-ethane / 2 h / 70 °C

With C₁₈H₃₃AuP⁽¹⁺⁾*BF₄^(1-); Dess-Martin periodane; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/anie.201604329

Reference yield: 100.0%

(S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate (1339021-76-9) → potassium (S)-7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate (1339022-13-7)

Guidance literature:

With potassium hydroxide; In water; acetonitrile; for 2h;

DOI:10.1021/ol202381m

Reference yield:

(S)-methyl 7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate (1339021-76-9) → (S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)(3-methylbut-2-enoyl)carbamate (1339021-85-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide / water; acetonitrile / 2 h

2.1: diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 0 °C

3.1: toluene / 1 h / 80 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 5 h / -78 °C / Inert atmosphere

With diphenylphosphoranyl azide; sodium hexamethyldisilazane; potassium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Curtius rearrangement;

DOI:10.1021/ol202381m

Downstream raw materials:

(S)-benzyl (7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizin-3-yl)(3-methylbut-2-enoyl)carbamate

(S)-3-amino-7a-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one

potassium (S)-7a-methyl-1-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate

C₉H₁₁NO₃