(3S,9aβ)-Octahydro-6α-(3-furyl)-9β-methyl-2H-quinolizine-3-methanol

Base Information

• Chemical Name: (3S,9aβ)-Octahydro-6α-(3-furyl)-9β-methyl-2H-quinolizine-3-methanol
• CAS No.: 6874-86-8
• Molecular Formula: C15H23NO2
• Molecular Weight: 249.353
• Mol file: 6874-86-8.mol

Synonyms:((9aS)-6t-[3]Furyl-9c-methyl-(9ar)-octahydro-chinolizin-3t-yl)-methanol;Castoramin;((3S,6S,9R,9aS)-6-Furan-3-yl-9-methyl-octahydro-quinolizin-3-yl)-methanol;(-)-Castoramin;((9aS)-6t-furan-3-yl-9c-methyl-(9ar)-octahydro-quinolizin-3t-yl)-methanol;((9aS)-6t-[3]furyl-9c-methyl-(9ar)-octahydro-quinolizin-3t-yl)-methanol;

Chemical Property of (3S,9aβ)-Octahydro-6α-(3-furyl)-9β-methyl-2H-quinolizine-3-methanol

Chemical Property:

• Boiling Point: 134 - 136 °C (0.2 mmHg)
• PSA: 36.61000
• LogP: 2.76140

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,9aβ)-Octahydro-6α-(3-furyl)-9β-methyl-2H-quinolizine-3-methanol

There total 26 articles about (3S,9aβ)-Octahydro-6α-(3-furyl)-9β-methyl-2H-quinolizine-3-methanol 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: 75.0%

C31H41NO2Si → (–)-castoramine (6874-86-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0037-1610435

Reference yield: 26.0%

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine (60161-30-0) → nupharolutine (38681-18-4) + (–)-castoramine (6874-86-8)

Guidance literature:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/jo048455k

Reference yield:

(S)-nipecotic acid (498-95-3,25137-00-2,59045-82-8,60252-41-7,262853-93-0) → (–)-castoramine (6874-86-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: thionyl chloride / 6 h / 100 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 14 h / 20 °C / Inert atmosphere

3.1: ruthenium (IV) oxide monohydrate; sodium periodate / water; ethyl acetate / 14 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

6.1: diphenylsilane; titanium(IV) isopropylate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

6.2: 2 h / -78 - 0 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Inert atmosphere; Reflux

9.1: Inert atmosphere

10.1: n-butyllithium / diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere

10.2: 1 h / 0 - 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; sodium periodate; n-butyllithium; thionyl chloride; ruthenium (IV) oxide monohydrate; diphenylsilane; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-0037-1610435

upstream raw materials:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine

(1R,9S)-1-methyl-7-methyleneoctahydro-4H-quinolizin-4-one

2(S)-[N-(p-toluenesulfonyl)-aziridin-2(S)-yl]-propan-1-ol

(1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide

Refernces

• 1、 Itabashi, Suguru,Shimomura, Masashi,Sato, Manabu,Azuma, Hiroki,Okano, Kentaro,Sakata, Juri,Tokuyama, Hidetoshi. "One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine". . p. 1786 - 1790. Retrieved 2018/07/03.