dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate
• CAS No.: 442202-09-7
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.395
• Mol file: 442202-09-7.mol

Synonyms:

Chemical Property of dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate

There total 16 articles about dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-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: 90.0%

vinyllithium (917-57-7) + dimethyl (5R,6S)-(+)-5-ethyl-6-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate (442202-08-6) → dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate (442202-09-7)

Guidance literature:

vinyllithium; With copper(l) iodide; In diethyl ether; at -78 - -35 ℃; for 0.333333h;

dimethyl (5R,6S)-(+)-5-ethyl-6-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate; In diethyl ether; at -78 - 0 ℃; for 1h; Further stages.;

DOI:10.1021/ol025775m

Reference yield: 90.0%

tetravinyltin (IV) (1112-56-7) + dimethyl (5R,6S)-(+)-5-ethyl-6-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate (442202-08-6) → dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate (442202-09-7)

Guidance literature:

tetravinyltin (IV); With methyllithium; In diethyl ether; at 0 ℃; for 0.5h;

With copper(l) iodide; In diethyl ether; at -78 - -35 ℃; for 0.333333h;

dimethyl (5R,6S)-(+)-5-ethyl-6-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate; In diethyl ether; at -78 - 0 ℃; for 1h;

DOI:10.1016/j.tet.2004.05.039

Reference yield:

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one (209257-75-0) → dimethyl (2S,3R,5R,6S)-(-)-5-ethyl-6-propyl-3-vinylpiperidine-1,2-dicarboxylate (442202-09-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 98 percent / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

2.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

3.1: 88 percent / Pd(PPh₃)4 / dimethylformamide / 15 h / 70 °C

4.1: MeLi / diethyl ether / 0.5 h / 0 °C

4.2: CuI / diethyl ether / 0.33 h / -78 - -35 °C

4.3: 96 percent / diethyl ether / 1 h / -78 - -30 °C

5.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

7.2: 691 mg / tetrahydrofuran; hexane / 2 h / 20 °C

8.1: H₂ / Pd-C / ethyl acetate / 48 h / 760 Torr

8.2: 77 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

10.1: NaH₂PO₄; 2-methyl-2-butene; aq. NaClO₂ / 2-methyl-propan-2-ol / 0.75 h / 20 °C

11.1: 1.008 g / ethyl acetate; diethyl ether / 20 h / 20 °C

12.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

12.2: 77 percent / PhSeCl / tetrahydrofuran; hexane / 20 h / 20 °C

13.1: MeLi / diethyl ether / 0.5 h / 0 °C

13.2: CuI / diethyl ether / 0.33 h / -78 - -35 °C

13.3: 90 percent / diethyl ether / 1 h / -78 - 0 °C

With sodium chlorite; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; methyllithium; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Swern oxidation / 7.2: Wittig reaction / 9.1: Swern oxidation;

DOI:10.1016/j.tet.2004.05.039

upstream raw materials:

tetravinyltin (IV)

dimethyl (5R,6S)-(+)-5-ethyl-6-propyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

vinyllithium

(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one