(2S)-6β-(3-Furanyl)-3α-methyl-2β-(3-methyl-2-butenyl)piperidine

Base Information

• Chemical Name: (2S)-6β-(3-Furanyl)-3α-methyl-2β-(3-methyl-2-butenyl)piperidine
• CAS No.: 4849-88-1
• Molecular Formula: C₁₅H₂₃NO
• Molecular Weight: 233.354
• Mol file: 4849-88-1.mol

Synonyms:

Chemical Property of (2S)-6β-(3-Furanyl)-3α-methyl-2β-(3-methyl-2-butenyl)piperidine

Chemical Property:

• Boiling Point: 113-115 °C(Press: 3 Torr)
• PKA: 9.54±0.10(Predicted)
• Density: 0.933±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-6β-(3-Furanyl)-3α-methyl-2β-(3-methyl-2-butenyl)piperidine

There total 15 articles about (2S)-6β-(3-Furanyl)-3α-methyl-2β-(3-methyl-2-butenyl)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:

(2S,3R)-6-Furan-3-yl-3-methyl-2-(3-methyl-but-2-enyl)-2,3,4,5-tetrahydro-pyridine → (-)-anhydronupharamine (4849-88-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; Yield given; Ambient temperature;

DOI:10.1039/c39940000499

Reference yield:

(4R,5R)-4-Methyl-5-(3-methyl-but-2-enyl)-dihydro-furan-2-one (140629-59-0) → (-)-anhydronupharamine (4849-88-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97.2 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.5 h / -78 °C

2.1: BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: p-toluenesulfonic acid / CH₂Cl₂ / 2 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.07 h / -78 °C

4.2: 92 percent / tetrahydrofuran / 0.25 h / -78 °C

5.1: 88 percent / diethyl azodicarboxylate; triphenylphosphine; diphenylphosphoryl azide / tetrahydrofuran / 3 h / 0 °C

6.1: triphenylphosphine / tetrahydrofuran / 3 h / Heating

7.1: sodium borohydride / ethanol / 1 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; diphenylphosphoranyl azide; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Reduction / 2.1: Ring cleavage / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Substitution / 6.1: Cyclization / 7.1: Reduction;

DOI:10.3987/COM-99-S26

Reference yield:

methyl (3S,4R)-4-(tert-butyldimethylsiloxy)-3,7-dimethyl-6-octenoate (144781-81-7) → (-)-anhydronupharamine (4849-88-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

2.1: 97.2 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.5 h / -78 °C

3.1: BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

4.1: p-toluenesulfonic acid / CH₂Cl₂ / 2 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.07 h / -78 °C

5.2: 92 percent / tetrahydrofuran / 0.25 h / -78 °C

6.1: 88 percent / diethyl azodicarboxylate; triphenylphosphine; diphenylphosphoryl azide / tetrahydrofuran / 3 h / 0 °C

7.1: triphenylphosphine / tetrahydrofuran / 3 h / Heating

8.1: sodium borohydride / ethanol / 1 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; 1.1: Cyclization / 2.1: Reduction / 3.1: Ring cleavage / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Ring cleavage / 6.1: Substitution / 7.1: Cyclization / 8.1: Reduction;

DOI:10.3987/COM-99-S26

upstream raw materials:

(4R,5R)-4-Methyl-5-(3-methyl-but-2-enyl)-dihydro-furan-2-one

methyl (3S,4R)-4-(tert-butyldimethylsiloxy)-3,7-dimethyl-6-octenoate

(1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(1-chloro-1-methyl-ethyl)-2-methyl-cyclopentanecarboxylic acid methyl ester

(4R,5R)-5-(3-methyl-2-butenyl)-4-methyl-2-hydroxytetrahydrofuran

Downstream raw materials:

1-benzoyl-6c-furan-3-yl-3c-methyl-2r-(3-methyl-but-2-enyl)-piperidine

Refernces

• 1、 Honda,Ishikawa,Yamane -i.. "A concise enantiospecific synthesis of nuphar piperidine alkaloids: Total synthesis of (-)-anhydronupharamine, (-)-nupharamine, (-)-nuphenine and (+)-3-epinupharamine". . p. 499 - 500. Retrieved 1994.
• 2、 Arata,Ohashi. "Constituents of Rhizoma nupharis. 23. The absolute configuration of nuphamine.". . p. 1365 - 1368. Retrieved 2007/10/07.