(-)-δ-Coniceine

Base Information

• Chemical Name: (-)-δ-Coniceine
• CAS No.: 89772-92-9
• Molecular Formula: C8H15N
• Molecular Weight: 125.214
• Mol file: 89772-92-9.mol

Synonyms:(-)-(R)-Indolizine;(R)-Octahydro-indolizine;(R)-(-)-indolizidine;(R)-(-)-coniceine;δ-(-)-coniceine;(-)-δ-coniceine;(8aR)-octahydroindolizine;

Chemical Property of (-)-δ-Coniceine

Chemical Property:

• PSA: 3.24000
• LogP: 1.57260

Purity/Quality:

(8aR)-octahydro-Indolizine 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-δ-Coniceine

There total 2 articles about (-)-δ-Coniceine 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:

(S)-1-Bromo-2-propyl-piperidine → coniine (458-88-8) + (-)-(8aR)-octahydroindolizine (89772-92-9)

Guidance literature:

With sulfuric acid; at 140 - 150 ℃; for 1.25h; Yields of byproduct given; 140 deg C - 150 deg C;

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (-)-(8aR)-octahydroindolizine (89772-92-9)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

2: sodium hydroxide / acetonitrile / 24 h / Heating

3: oxone (R) / methanol; H₂O / 12 h / 20 °C

4: 60 percent / sodium hydride / dimethylformamide / 4 h / 0 °C

5: 51 percent / sodium amalgam; Na₂HPO₄ / methanol / 48 h / 20 °C

6: 85 percent / lithium aluminum hydride / diethyl ether / 24 h / 20 °C

With dmap; Oxone; sodium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; sodium hydride; triethylamine; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(01)00377-9

Reference yield:

(-)-(8aR)-octahydroindolizine (89772-92-9) → (octahydro-indolizin-3-yl)-diphenyl-methanol

Guidance literature:

Multi-step reaction with 2 steps

1.1: BF₃*OEt₂ / diethyl ether / 0.5 h / 0 °C

2.1: s-BuLi; TMEDA / diethyl ether / 2 h / -78 °C

2.2: 18 percent / diethyl ether / 0.75 h / -78 - -30 °C

With N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; In diethyl ether;

DOI:10.1021/ja0675144

upstream raw materials:

(S)-Pyroglutaminol

Downstream raw materials:

(R)-(-)-coniceine picrate