(S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester
• CAS No.: 690224-49-8
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304
• Mol file: 690224-49-8.mol

Synonyms:(S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester

Chemical Property of (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester

There total 1 articles about (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester 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:

danishefsky's diene (54125-02-9) + ethyl (E)-2-(p-methoxyphenylimino)acetate (115276-75-0,124156-21-4,120419-96-7) → (R)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester + (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester (690224-49-8)

Guidance literature:

With CuClO₄*4MeCN; Tol-BINAP-(R); In dichloromethane; at 20 ℃; for 20h; Further Variations:; Solvents; Temperatures; Product distribution;

DOI:10.1002/1521-3765(20000703)6:13<2435::AID-CHEM2435>3.0.CO;2-Z

Reference yield:

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester (690224-49-8) → (S)-1-(4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid ethyl ester (911705-05-0)

Guidance literature:

(S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester; With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h;

N,N-phenylbistrifluoromethane-sulfonimide; In tetrahydrofuran; at -78 - 0 ℃;

Reference yield:

(S)-N-p-Methoxyphenyl-4-oxo-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid ethyl ester (690224-49-8) → [(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetonitrile (911705-64-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

1.2: -78 - 20 °C

2.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; ethanol; water / 3 - 6 h / 75 °C

3.1: borane-THF / tetrahydrofuran / 2 - 6 h / 40 °C

4.1: trifluorormethanesulfonic acid / dichloromethane / 3 h / -30 - 0 °C

5.1: ammonium cerium(IV) nitrate; water / acetonitrile / 0.5 h / 0 °C

6.1: borane-THF / tetrahydrofuran / 2 - 8 h / 50 °C

7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

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

8.2: 0 - 20 °C

9.1: triethylamine / dichloromethane / 1 h / 0 °C

10.1: dimethyl sulfoxide / 4 h / 50 °C

With dmap; lithium aluminium tetrahydride; borane-THF; ammonium cerium(IV) nitrate; trifluorormethanesulfonic acid; water; L-Selectride; sodium carbonate; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

danishefsky's diene

ethyl (E)-2-(p-methoxyphenylimino)acetate

Downstream raw materials:

(S)-1-(4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid ethyl ester

(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-2-carboxylic acid ethyl ester

(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-2-carboxylic acid ethyl ester

(S)-1,4-bis-(4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid ethyl ester