(R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

Base Information

• Chemical Name: (R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate
• CAS No.: 435275-85-7
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• DSSTox Substance ID: DTXSID50582129
• Nikkaji Number: J2.383.907E
• Wikidata: Q82473453
• Mol file: 435275-85-7.mol

Synonyms:435275-85-7;(R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate;(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER 3-ETHYL ESTER;1-O-benzyl 3-O-ethyl (3R)-piperidine-1,3-dicarboxylate;1-Benzyl 3-ethyl (3R)-piperidine-1,3-dicarboxylate;SCHEMBL3271535;DTXSID50582129;NJRONXOELMBCSE-CQSZACIVSA-N;MFCD07374391;AKOS015923340;AS-41654;CS-0452542;1-Benzyl 3-ethyl (R)-piperidine-1,3-dicarboxylate;(r)-piperidine-1,3-dicarboxylic acid 1-benzyl 3-ethyl ester;(3R)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

Chemical Property of (R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

Chemical Property:

• PSA: 55.84000
• LogP: 2.53620
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 352

Purity/Quality:

98%min ^*data from raw suppliers

(R)-PIPERIDINE-1,3-DICARBOXYLIC ACID-1-BENZYL ESTER-3-ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCN(C1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@@H]1CCCN(C1)C(=O)OCC2=CC=CC=C2

Technology Process of (R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

There total 5 articles about (R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate 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:

5,6-dihydro-4H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (917112-56-2) → (3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (174699-11-7) + (R)-N-Cbz-ethyl nipecotate (435275-85-7)

Guidance literature:

With hydrogen; [Rh((S,S,R,R)-Tangphos)NBD][SbF₆]; In dichloromethane; at 80 ℃; for 72h; under 77572.2 Torr; Title compound not separated from byproducts;

DOI:10.1002/ejoc.200600558

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + Ethyl nipecotate (71962-74-8) → (3S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (174699-11-7) + (R)-N-Cbz-ethyl nipecotate (435275-85-7)

Guidance literature:

With triethylamine; In dichloromethane; at 15 - 25 ℃; for 16h; Overall yield = 58 %; Overall yield = 313 mg;

DOI:10.1021/acs.orglett.8b00864

Reference yield:

3-pyridinecarboxylic acid ethyl ester (614-18-6) → (R)-N-Cbz-ethyl nipecotate (435275-85-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / 5 percent Pd-C / aq. ethanol / 36 h / 20 °C / 5171.48 Torr

2: BuLi / -78 °C

3: H₂ / [Rh((S,S,R,R)-Tangphos)NBD][SbF₆] / CH₂Cl₂ / 72 h / 80 °C / 77572.2 Torr

With n-butyllithium; hydrogen; palladium on activated charcoal; [Rh((S,S,R,R)-Tangphos)NBD][SbF₆]; In ethanol; dichloromethane;

DOI:10.1002/ejoc.200600558

upstream raw materials:

5,6-dihydro-4H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

3-pyridinecarboxylic acid ethyl ester

ethyl 1,4,5,6-tetrahydropyridine-3-carboxylate

benzyl chloroformate

Downstream raw materials:

benzyl 3-(hydroxymethyl)-1-piperidinecarboxylate

Refernces

• 1、 Lei, Aiwen,Chen, Mao,He, Minsheng,Zhang, Xumu. "Asymmetric hydrogenation of pyridines: Enantioselective synthesis of nipecotic acid derivatives". . p. 4343 - 4347. Retrieved 2007/10/03.