(3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

Base Information

• Chemical Name: (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone
• CAS No.: 173095-49-3
• Molecular Formula: C₂₂H₂₁NO₅
• Molecular Weight: 379.412
• Mol file: 173095-49-3.mol

Synonyms:(3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

Chemical Property of (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

There total 1 articles about (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone 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: 47.0%

Diethyl (S)-malate (691-84-9) + phenylpropargylidene p-anisidine (106318-93-8) → (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone (173095-49-3) + (3S,4R,5R)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

Guidance literature:

Diethyl (S)-malate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

phenylpropargylidene p-anisidine; In tetrahydrofuran; at -78 - 0 ℃; for 1.5h; Further stages.;

DOI:10.1021/jo0012187

Reference yield: 91.0%

(3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone (173095-49-3) → (3S,4S,5S)-3-hydroxy-4-hydroxymethyl-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone (321887-26-7)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In diethylene glycol dimethyl ether; at 20 ℃; for 24h;

DOI:10.1021/jo0012187

Reference yield:

(3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone (173095-49-3) → (1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine (321887-52-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 91 percent / NaBH₄; LiCl / bis-(2-methoxy-ethyl) ether / 24 h / 20 °C

2.1: NaH / dimethylformamide / 0.5 h

2.2: 86 percent / 1 h / 20 °C

3.1: 85 percent / H₂ / Lindlar catalyst / benzene / 0.67 h / 2068.65 Torr

4.1: 77 percent / CAN / acetonitrile / 1 h / 0 °C

5.1: 95 percent / NaH; nBu₄NI / tetrahydrofuran / 1 h / 20 °C

6.1: 90 percent / Grubbs catalyst / benzene / 12 h / Heating

7.1: 61 percent / NaHCO₃; m-CPBA / benzene / 36 h / 20 °C

8.1: 65 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

9.1: 70 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 16 h / 20 °C

10.1: 70 percent / K₂CO₃; H₂O / methanol; tetrahydrofuran / 4 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium chloride; diethylazodicarboxylate; Lindlar's catalyst; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo0012187

upstream raw materials:

Diethyl (S)-malate

phenylpropargylidene p-anisidine

Downstream raw materials:

(3S,4S,5S)-3-hydroxy-4-hydroxymethyl-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone

(1S,2S,7R,7aS)-2-benzyloxy-1-benzyloxymethyl-7-hydroxy-7a-pyrrolizidine

(1S,2S,7aR)-2-benzyloxy-1-benzyloxymethyl-2,5,7a-trihydropyrrolizin-3-one

(1aS,5S,6S,6aS,6bR)-5-benzyloxy-6-benzyloxymethylperhydrooxireno[2,3-a]pyrrolizin-4-one