1-Epilupinine

Base Information

• Chemical Name: 1-Epilupinine
• CAS No.: 486-71-5
• Molecular Formula: C10H19 N O
• Molecular Weight: 169.267
• DSSTox Substance ID: DTXSID901318170
• Nikkaji Number: J37.655H
• Wikidata: Q104250353
• Mol file: 486-71-5.mol

Synonyms:1S-cis-octahydro-2H-quinolizine-1-methanol;epilupinine;lupinine;lupinine hydrochloride, (1R-trans)-isomer;lupinine, (1S-cis)-isomer;octahydroquinolizine-1-methanol

Chemical Property of 1-Epilupinine

Chemical Property:

• Melting Point: 77-78 °C
• Boiling Point: 270°Cat760mmHg
• PKA: 14.90±0.10(Predicted)
• Flash Point: 99.1°C
• PSA: 23.47000
• Density: 1.04g/cm³
• LogP: 1.18110
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.146664230
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCC(C2C1)CO
• Isomeric SMILES: C1CCN2CCC[C@@H]([C@H]2C1)CO
• General Description: 1-Epilupinine is a quinolizidine alkaloid that can be efficiently synthesized via an intramolecular nitrile oxide-alkene cycloaddition (INOC) as a key step, enabling the construction of its quinolizidine skeleton. A novel method was developed to prepare a critical intermediate, (R)-(2-vinylpiperid-1-yl)propanal oxime, avoiding unstable aldehyde intermediates through a two-step Mitsunobu reaction and N-detosylation. The synthesis concludes with Raney nickel-mediated desulfurization, yielding (+)-Epilupinine in a scalable and practical manner, while also demonstrating broader applicability for synthesizing related alkaloids.

Technology Process of 1-Epilupinine

There total 59 articles about 1-Epilupinine 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: 94.0%

tert-butyl (1S,9aR)-octahydro-1H-quinolizine-1-carboxylate (1032169-38-2) → (+)-epilupinine (486-71-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 10h; Reflux;

DOI:10.1021/ol800722a

Reference yield: 90.0%

(1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine (138713-63-0) → (+)-epilupinine (486-71-5)

Guidance literature:

With nickel; In ethanol; at 25 ℃; for 10h;

DOI:10.1055/s-1991-26620

Reference yield: 72.0%

Ethyl (1S,9aR)-Octahydro-2H-quinolizine-1-carboxylate (28270-22-6) → (+)-epilupinine (486-71-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 25 ℃; for 8h;

DOI:10.1055/s-1991-26620

upstream raw materials:

lupinine

3-(2(S)-(6-oxo-2(R)-piperidinyl)-5-chlorovaleryl)-4(R)-isopropyl-1,3-thiazolidine-2-thione

Ethyl (1S,9aR)-Octahydro-2H-quinolizine-1-carboxylate

(1R,9aR)-Octahydro-1-hydroxymethyl-1-<(S)-(4-methylphenyl)sulfinyl>-2H-quinolizine

Downstream raw materials:

1-phenyl-2-(quinolizidin-1β-yl)ethanone

Refernces

Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition

10.1021/jo101910r

The study presents a nine-step total synthesis of the quinolizidine alkaloid (+)-Epilupinine with an overall yield of 48%. The key step in this synthesis is the intramolecular nitrile oxide-alkene cycloaddition (INOC), which is used to construct the quinolizidine skeleton. The researchers developed a novel method to efficiently prepare the challenging intermediate (R)-(2-vinylpiperid-1-yl)propanal oxime (13a) from (R)-(2-vinylpiperid-1-yl)propanol (11a) using a two-step process involving Mitsunobu reaction and N-detosylation, avoiding the use of the highly unstable aldehyde intermediate. This method was further generalized to convert various 3-(N,N-dialkylamino)propanols into their corresponding oximes. The final steps of the synthesis involve a Raney nickel-promoted desulfurization to yield the target compound (+)-Epilupinine. The study not only provides a practical and scalable route to this biologically important alkaloid but also offers a new approach for the application of INOC in the total synthesis of other alkaloids.