Benzyl (+/-)-trans-4-methyl-piperidine-2-carboxylate

Base Information

• Chemical Name: Benzyl (+/-)-trans-4-methyl-piperidine-2-carboxylate
• CAS No.: 339183-94-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• DSSTox Substance ID: DTXSID00432544
• Nikkaji Number: J1.483.262I
• Wikidata: Q82246612
• Mol file: 339183-94-7.mol

Synonyms:BENZYL (+/-)-TRANS-4-METHYL-PIPERIDINE-2-CARBOXYLATE;339183-94-7;Benzyl (2R,4R)-4-methylpiperidine-2-carboxylate;SCHEMBL1576471;trans-4-Methyl-piperidine-2-carboxylic acid benzyl ester;DTXSID00432544;CS-0451364;Benzyl(+/-)-trans-4-methyl-piperidine-2-carboxylate;4alpha-Methylpiperidine-2beta-carboxylic acid benzyl ester

Chemical Property of Benzyl (+/-)-trans-4-methyl-piperidine-2-carboxylate

Chemical Property:

• PSA: 38.33000
• LogP: 2.44670
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

Benzyl(+/-)-trans-4-methyl-piperidine-2-carboxylate 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCNC(C1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1CCN[C@H](C1)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl (+/-)-trans-4-methyl-piperidine-2-carboxylate

There total 6 articles about Benzyl (+/-)-trans-4-methyl-piperidine-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: 100.0%

benzyl trans-N-Boc-4-methylpipecolic acid ester (339183-92-5) → trans-benzyl 4-methylpipecolic acid ester (339183-94-7)

Guidance literature:

With hydrogenchloride; In ethyl acetate;

DOI:10.1016/S0040-4039(01)00138-1

Reference yield:

4-methylpiperidine-1-carboxylic acid tert-butyl ester (123387-50-8) → trans-benzyl 4-methylpipecolic acid ester (339183-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: s-BuLi; TMEDA / diethyl ether / -90 °C

1.2: 35 percent / diethyl ether / -90 - 20 °C

2.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C

With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; ethyl acetate;

DOI:10.1016/S0960-894X(01)00351-1

Reference yield:

4-methylpiperidin (626-58-4) → trans-benzyl 4-methylpipecolic acid ester (339183-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: s-BuLi; TMEDA / diethyl ether / -90 °C

2.2: 35 percent / diethyl ether / -90 - 20 °C

3.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C

With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; triethylamine; In diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(01)00351-1

upstream raw materials:

benzyl trans-N-Boc-4-methylpipecolic acid ester

4-methylpiperidin

4-methylpiperidine-1-carboxylic acid tert-butyl ester

benzyl chloroformate