(+/-)-buphanisine

Base Information

• Chemical Name: (+/-)-buphanisine
• CAS No.: 124093-57-8
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.343
• Mol file: 124093-57-8.mol

Synonyms:

Chemical Property of (+/-)-buphanisine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-buphanisine

There total 10 articles about (+/-)-buphanisine 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: 62.0%

crinine (909263-42-9) + diazomethyl-trimethyl-silane (18107-18-1) → buphanisine (468-22-4,6835-79-6,111958-06-6,124093-57-8)

Guidance literature:

With tetrafluoroboric acid; In dichloromethane; for 36h;

DOI:10.1039/c7sc02112g

Reference yield:

4-<2-<<(allyloxy)carbonyl>benzylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (111923-06-9) → (+/-)-buphanisine (468-22-4,6835-79-6,111958-06-6,124093-57-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / Ph₃P, Bu(Et)CHCO₂H / Pd(Ph₃P)4 / CH₂Cl₂ / 48 h / Ambient temperature

2: AlH₃ / tetrahydrofuran

3: 1.) Ms₂O, Et₃N

4: 95 percent / 1.) ACE-Cl; 2.) MeOH / 1.) ClCH₂CH₂Cl, Proton Sponge, reflux, 3 h; 2.) reflux, 2 h

5: 1.) 40percent aq. CH₂O; 2.) 6N HCl / 1.) MeOH, RT, 10 min; 2.) RT, 3 h

With aluminium hydride; hydrogenchloride; methanol; formaldehyd; 2-Ethylhexanoic acid; carbonochloridic acid 1-chloro-ethyl ester; triethylamine; triphenylphosphine; Methanesulfonic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)95766-6

Reference yield:

→ buphanisine (468-22-4,6835-79-6,111958-06-6,124093-57-8)

Guidance literature:

With i-Amyl alcohol; sodium; xylene;

DOI:10.1021/ja01549a073

upstream raw materials:

(+/-)-oxo-crinine

crinine

diazomethyl-trimethyl-silane

(3aS*,6R*,7aR*)-3a-<3,4-(methylenedioxy)phenyl>-6-methoxy-2,3,3a,6,7,7a-hexahydro-1H-indole