(S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate
• CAS No.: 1407965-69-8
• Molecular Formula: C₁₇H₂₁NO₅
• Molecular Weight: 319.357
• Mol file: 1407965-69-8.mol

Synonyms:(S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

Chemical Property of (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate

There total 4 articles about (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-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: 92.0%

?(S)-benzyl 2-(1-hydroxyallyl)pyrrolidine-1-carboxylate + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate (1407965-69-8)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2012.08.061

Reference yield:

benzyl (S)-2-{[methoxy(methyl)amino]carbonyl}pyrrolidine-1-carboxylate (146118-95-8) → (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate (1407965-69-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

2: tetrahydrofuran / 3 h / 0 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; In tetrahydrofuran; toluene;

DOI:10.1016/j.tetlet.2012.08.061

Reference yield:

(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester (71461-30-8) → (S)-E-benzyl 2-(1-hydroxy-4-methoxy-4-oxobut-2-en-1-yl)pyrrolidine-1-carboxylate (1407965-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / 0 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; toluene;

DOI:10.1016/j.tetlet.2012.08.061

upstream raw materials:

N-Benzyloxycarbonyl-L-proline

acrylic acid methyl ester

benzyl (S)-2-{[methoxy(methyl)amino]carbonyl}pyrrolidine-1-carboxylate

(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

(S)-benzyl 2-((2S,3R,4R)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate

(5R,6S)-5-hydroxyazabicyclo[4.3.0]nonan-2-one

(8S,8aS)-8-hydroxyhexahydroindolizin-5(1H)-one