N-benzyl-6α-methoxycarbonylcytisine

Base Information

• Chemical Name: N-benzyl-6α-methoxycarbonylcytisine
• CAS No.: 474116-12-6
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.406
• Mol file: 474116-12-6.mol

Synonyms:N-benzyl-6α-methoxycarbonylcytisine

Chemical Property of N-benzyl-6α-methoxycarbonylcytisine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-6α-methoxycarbonylcytisine

There total 2 articles about N-benzyl-6α-methoxycarbonylcytisine 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: 65.0%

benzyl bromide (100-39-0) + (-)-N-methoxycarbonyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (125109-97-9) → N-benzyl-6α-methoxycarbonylcytisine (474116-12-6)

Guidance literature:

(-)-N-methoxycarbonyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

DOI:10.1016/S0957-4166(02)00271-9

Reference yield:

cytisine (485-35-8) → N-benzyl-6α-methoxycarbonylcytisine (474116-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / triethylamine / CH₂Cl₂ / 20 °C

2.1: lithium diisopropylamide; LiCl / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 65 percent / tetrahydrofuran; hexane / 3 h / -78 °C

With triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0957-4166(02)00271-9

Reference yield: 57.0%

N-benzyl-6α-methoxycarbonylcytisine (474116-12-6) → N-benzyl-6β-methoxycarbonylcytisine

Guidance literature:

With 18-crown-6 ether; sodium hydride; In tetrahydrofuran; for 72h;

DOI:10.1016/S0957-4166(02)00271-9

upstream raw materials:

benzyl bromide

(-)-N-methoxycarbonyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

cytisine