methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

Base Information

• Chemical Name: methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate
• CAS No.: 282527-09-7
• Molecular Formula: C₁₃H₁₄N₂O₆S
• Molecular Weight: 326.33
• Mol file: 282527-09-7.mol

Synonyms:methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

Chemical Property of methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

There total 3 articles about methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-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: 88.0%

methyl (2S)-6-benzyloxy-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate (282527-08-6) → methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate (282527-09-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1039/b001253j

Reference yield:

methyl (S)-2-(4-nitrobenzenesulfonylamino)pent-4-enoate → methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate (282527-09-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Et₃N / Pd(OAc)2/dppp / acetonitrile / 16 h / 20 °C

2: 89 percent / RuCl₂[PCy₃]2[=CHPh] / CH₂Cl₂ / 16 h / 20 °C

3: 88 percent / triethylsilane; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

With triethylsilane; boron trifluoride diethyl etherate; triethylamine; palladium diacetate; Grubbs catalyst first generation; 1,3-bis-(diphenylphosphino)propane; In dichloromethane; acetonitrile;

DOI:10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO;2-8

Reference yield:

methyl 2-[(1-benzyloxyallyl)-(4-nitrobenzenesulfonyl)amino]-(S)-pent-4-enoate (282527-06-4) → methyl (S)-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate (282527-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / RuCl₂[PCy₃]2[=CHPh] / CH₂Cl₂ / 16 h / 20 °C

2: 88 percent / triethylsilane; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

With triethylsilane; boron trifluoride diethyl etherate; Grubbs catalyst first generation; In dichloromethane;

DOI:10.1002/1615-4169(200208)344:6/7<736::AID-ADSC736>3.0.CO;2-8

upstream raw materials:

methyl (2S)-6-benzyloxy-1-(4-nitrobenzenesulfonyl)-1,2,3,6-tetrahydropyridine-2-carboxylate

methyl 2-[(1-benzyloxyallyl)-(4-nitrobenzenesulfonyl)amino]-(S)-pent-4-enoate

Downstream raw materials:

(2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid

(S)-methyl 1,2,3,6-tetrahydropyridine-2-carboxylate