(R)-3-Methylpiperidine

Base Information

• Chemical Name: (R)-3-Methylpiperidine
• CAS No.: 16078-25-4
• Molecular Formula: C6H13N
• Molecular Weight: 99.17410
• DSSTox Substance ID: DTXSID90423805
• Nikkaji Number: J825.515F
• Wikidata: Q72495728
• Mol file: 16078-25-4.mol

Synonyms:(R)-3-Methylpiperidine;16078-25-4;(3R)-3-methylpiperidine;(R)-3-Methyl-piperidine;Piperidin, 3e-methyl;(R)-(-)-3-Methyl-piperidine;MFCD08448245;(R)-(-)-3-METHYLPIPERIDINE;Piperidine, 3-methyl-, (3R)-;3alpha-Methylpiperidine;r-(-)-3-methylpiperidine;DTXSID90423805;JEGMWWXJUXDNJN-ZCFIWIBFSA-N;AKOS006348098;AS-59629;CS-0056870;EN300-211248;F14484;A858038

Chemical Property of (R)-3-Methylpiperidine

Chemical Property:

• Boiling Point: 125℃
• PKA: 10.49±0.10(Predicted)
• Flash Point: 17℃
• PSA: 12.03000
• Density: 0.809
• LogP: 1.33470
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 99.104799419
• Heavy Atom Count: 7
• Complexity: 52.1

Purity/Quality:

NLT 98% ^*data from raw suppliers

(R)-3-Methylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCNC1
• Isomeric SMILES: C[C@@H]1CCCNC1

Technology Process of (R)-3-Methylpiperidine

There total 6 articles about (R)-3-Methylpiperidine 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: 72.0%

2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate + 3-Methylpiperidine (626-56-2,53152-98-0) → (R,R)-3-methyl-1-(2-phenoxypropanoyl)piperidine + (R)-3-methyl-1-(2-phenoxypropanoyl)piperidine + (-)-(R)-3-methylpiperidine (16078-25-4) + (+)-(S)-3-methylpiperidine (17305-22-5)

Guidance literature:

In toluene; for 24h; stereoselective reaction;

DOI:10.1039/d1ob02099d

Reference yield: 22.0%

2-methylcadaverine (15520-10-2) → (-)-(R)-3-methylpiperidine (16078-25-4)

Guidance literature:

With R-selective imine reductase from streptosporangium roseum; NAD⁺-reducing hydrogenase from Ralstonia eutropha H₁₆, variant E₃₄₁A/S₃₄₂R; putrescine oxidase from Rhodococcus erythropolis, variant E₂₀₃G; water; hydrogen; oxygen; NADPH; catalase; In aq. buffer; at 25 ℃; for 0.5h; pH=7.5;

DOI:10.1039/c8gc03798a

Reference yield:

(S)-4-isopropyl-3-(5-methylpyridin-2-yl)oxazolidin-2-one (737760-90-6) → (-)-(R)-3-methylpiperidine (16078-25-4) + (+)-(S)-3-methylpiperidine (17305-22-5)

Guidance literature:

With hydrogen; acetic acid; Rh-Pd on carbon; at 20 ℃; for 20h; under 75006 Torr; Further Variations:; Catalysts; Product distribution;

DOI:10.1002/anie.200453942

upstream raw materials:

3-Methylpiperidine

(S)-4-isopropyl-3-(5-methylpyridin-2-yl)oxazolidin-2-one

2-methylcadaverine

Downstream raw materials:

(-)-(R)-N-benzoyl-3-methylpiperidine

(3R)-3-methyl-1,4'-bipiperidine

Refernces

• 1、 Bartashevich, Ekaterina V.,Chulakov, Evgeny N.,Ezhikova, Marina A.,Gruzdev, Dmitry A.,Kodess, Mikhail I.,Korolyova, Marina A.,Krasnov, Victor P.,Levit, Galina L.,Tumashov, Andrey A.,Vakarov, Sergey A.. "Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate". supporting information. p. 862 - 869. Retrieved 2022/02/03.
• 2、 Sliwka, Hans-Richard,Hansen, Hans-Juergen. "First Direct Synthesis of Optically Active 3-Methylcyclopentene". . p. 434 - 440. Retrieved 2007/10/02.