(2R,6R)-2-methyl-6-prop-1-enyl-piperidine

Base Information

• Chemical Name: (2R,6R)-2-methyl-6-prop-1-enyl-piperidine
• CAS No.: 501-02-0
• Molecular Formula: C₉H₁₇N
• Molecular Weight: 139.241
• Mol file: 501-02-0.mol

Synonyms:Pinidine(6CI,7CI,8CI); Piperidine, 2-methyl-6-(1-propenyl)-, [2R-[2a,6a(E)]]-; Piperidine, 2-methyl-6-(1E)-1-propenyl-,(2R,6R)- (9CI); (-)-Pinidine; cis-(-)-6-Propenyl-2-pipecoline

Chemical Property of (2R,6R)-2-methyl-6-prop-1-enyl-piperidine

Chemical Property:

• Vapor Pressure: 0.779mmHg at 25°C
• Boiling Point: 183.2°Cat760mmHg
• Flash Point: 56.1°C
• PSA: 12.03000
• Density: 0.879g/cm³
• LogP: 2.42190

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A piperidine alkaloid isolated from Pinus jeffreyi, P. sabiniana Doug!., and P. torreyana, this base is a colourless liquid which is laevorotatory with [Ql~~9 - 10.5° and [Ql~j5 - 23.4° (c 1.88, EtOH). It yields a crystalline hydrochloride as colourless needles from EtOH-AcOEt, m.p. 244-6°C and a methiodide, m.p. 214-8°C. The structure has been determined by spectroscopic methods as 2-methyl-6-( trans-2-propeny I)-piperidine.

Technology Process of (2R,6R)-2-methyl-6-prop-1-enyl-piperidine

There total 61 articles about (2R,6R)-2-methyl-6-prop-1-enyl-piperidine 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: 81.0%

(2R,6R)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine (117941-17-0) → (-)-pinidine (501-02-0)

Guidance literature:

With ammonia; sodium; In ethanol; at -78 ℃;

DOI:10.1016/0040-4039(96)00990-2

Reference yield: 70.0%

(2R,6R,1'R)-N-(2'-hydroxy-1'-phenylethyl)-2-(1-propynyl)-6-methylpiperidine → (-)-pinidine (501-02-0)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 9h;

DOI:10.1021/jo971127i

Reference yield:

(2S,3R)-2,3-Bis<(methoxymethyl)oxy>-8-nonen-4-one (117941-18-1) → (-)-pinidine (501-02-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C

2: 57 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

3: hydrazine hydrate / ethanol / 2.5 h / Heating

4: aq. Na₂CO₃ / CH₂Cl₂ / 3 h / Heating

5: 68 percent / O₂, PdCl₂, CuCl₂ / dimethylformamide; H₂O / 0.67 h / 70 °C

6: 95 percent / H₂ / 10percent Pd/C / methanol / 1 h

7: 51 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / Ambient temperature

8: 85 percent / concentrated HCl / methanol / 0.5 h / Heating

9: 88 percent / diisopropylethylamine / CH₂Cl₂ / 2 h / Heating

10: 89 percent / trimethyl phosphite / 14 h / Heating

11: 79 percent / liquid ammonia, Na / ethanol / 14 h / Ambient temperature

With hydrogenchloride; ammonia; hydrogen; oxygen; sodium; L-Selectride; sodium carbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper dichloride; palladium dichloride; diethylazodicarboxylate; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00186a038

upstream raw materials:

(2R,6R)-6-Methyl-2-<(E)-1-propenyl>-N-(p-tolylsulfonyl)piperidine

(2R,6R)-2-((E)-3-Methoxymethoxy-propenyl)-6-methyl-piperidine-1-carboxylic acid benzyl ester

(2R,6R)-1-<(benzyloxy)methoxy>-2-methyl-6-<(E)-prop-1'-enyl>piperidine

9-azabicyclo<3.3.1>nonan-3-one hydrochloride

Refernces

• 1、 Hong, Sukwon,Marks, Tobin J.. "Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides". . p. 7886 - 7887. Retrieved 2007/10/03.
• 2、 Kirihara, Masayuki,Nishio, Takashi,Yokoyama, Satoshi,Kakuda, Hiroko,Momose, Takefumi. "Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids". . p. 2911 - 2926. Retrieved 2007/10/03.