1,3(2H)-Pyridinedicarboxylic acid, 5,6-dihydro-4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-ethyl ester

Base Information

• Chemical Name: 1,3(2H)-Pyridinedicarboxylic acid, 5,6-dihydro-4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-ethyl ester
• CAS No.: 532977-39-2
• Molecular Formula: C21H30N2O4
• Molecular Weight: 374.48
• Mol file: 532977-39-2.mol

Synonyms:

Chemical Property of 1,3(2H)-Pyridinedicarboxylic acid, 5,6-dihydro-4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3(2H)-Pyridinedicarboxylic acid, 5,6-dihydro-4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-ethyl ester

There total 6 articles about 1,3(2H)-Pyridinedicarboxylic acid, 5,6-dihydro-4-[[(1R)-1-phenylethyl]amino]-, 1-(1,1-dimethylethyl) 3-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: 97.0%

(R)-1-phenyl-ethyl-amine (3886-69-9) + 1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate (98977-34-5) → 4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (532977-39-2)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 140 ℃; for 18h; Dean-Stark;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + C9H14O3NC6H5 (41276-30-6) + (R)-1-phenyl-ethyl-amine (3886-69-9) → 4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (532977-39-2)

Guidance literature:

C₉H₁₄O₃NC₆H₅; With ammonium formate; palladium over charcoal;

di-tert-butyl dicarbonate;

(R)-1-phenyl-ethyl-amine;

Reference yield:

ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (1454-53-1) → 4-((R)-1-phenylethylamino)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (532977-39-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / HCO₂NH₄ / Pd/C / ethanol / 1 h / Heating

2: NaHCO₃; NaCl / CHCl₃; H₂O / 15 h / Heating

3: 13.7 g / p-TsOH / benzene / 7 h / Heating

With ammonium formate; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium chloride; palladium on activated charcoal; In ethanol; chloroform; water; benzene;

DOI:10.1002/ejoc.200390112

upstream raw materials:

(R)-1-phenyl-ethyl-amine

1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate

4-piperidone-3-carboxylic acid ethyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(3R,4R)-4-((R)-1-phenylethylamino)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

1-(tert-butyl) 3-ethyl (3S,4R)-4-(((R)-1-phenylethyl)amino)piperidine-1,3-dicarboxylate

4-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4R)-1-(tert-butoxycarbonyl)-4-((R)-1-phenylethylamino)piperidine-3-carboxylic acid