(+/-)-schelhammeridine

Base Information

• Chemical Name: (+/-)-schelhammeridine
• CAS No.: 129112-79-4
• Molecular Formula: C₁₉H₂₁NO₃
• Molecular Weight: 311.381
• Mol file: 129112-79-4.mol

Synonyms:

Chemical Property of (+/-)-schelhammeridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-schelhammeridine

There total 48 articles about (+/-)-schelhammeridine 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:

(+/-)-8-oxoschelhammeridine (24204-40-8,129172-79-8,129172-80-1) → (+/-)-schelhammeridine (22373-00-8,24204-35-1,129112-79-4,129112-98-7)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride;

DOI:10.3987/COM-89-S49

Reference yield:

8-oxo-3-epischelhammeridine (24204-40-8,129172-79-8,129172-80-1) → (+/-)-epischelhammeridine (22373-00-8,24204-35-1,129112-79-4,129112-98-7)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride;

DOI:10.3987/COM-89-S49

Reference yield:

2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-2-benzodiazepine-1-thione (102487-69-4) → (+/-)-epischelhammeridine (22373-00-8,24204-35-1,129112-79-4,129112-98-7)

Guidance literature:

Multi-step reaction with 21 steps

1: 2.) triphenylphosphine, potassium tert-butoxide / 1.) CH₃CN, RT, 17 h 2.) DMF, reflux, 8 h

2: 93 percent / diethyl ether / 2 h / 0 °C

3: 80 percent / acetonitrile / 0.33 h / 0 °C / Irradiation

4: 100 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5: 89 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.75 h / -30 °C

6: 100 percent / H₂ / 10percent Pd/C / tetrahydrofuran; acetone / 3 h / 2942.03 Torr / Ambient temperature

7: 95 percent / DMSO, acetic anhydride / 17 h / Ambient temperature

8: 99 percent / p-TsOH / benzene / 4 h / Heating

9: 82 percent / MgCl₂, tert-heptylmercaptan / dimethylsulfoxide / 3 h / 160 °C

10: 94 percent / NaBH₄ / tetrahydrofuran; methanol / 1.) 0 deg C, 1 h, 2.) RT, 3 h

11: 100 percent / 5percent aq. HCl / acetone / 3 h / 70 °C

12: 4-dimethylaminopyridine, pyridine / 2 h / 0 °C

13: 5percent K₂CO₃ / methanol / 1 h / 75 °C

14: 1.) PhSeCl, BF₃*Et₂O, 2.) mercury(II) perchlorate(MPC) / 1.) THF, reflux, 1 h, 2.) MeOH, 65 deg C, 30 min

15: 100 percent / NaBH₄ / methanol / 0.5 h / 0 °C

16: 1.) NaH, imidazole / 1.) THF, reflux, 1 h, 2.) THF, reflux, 30 min

17: n-Bu3SnH, α,α-azobisisobutyronitrile (AIBN) / toluene / 0.67 h / Heating

18: 1.) CeCl₃*6H₂O, NaBH₄, 2.) NaH, imidazole, 3.) n-Bu₄nHSO₄

19: 1.) lithium diisopropylamide, n-BuLi / 1.) THF, hexane -78 deg C, 30 min, 2.) THF, hexane, 1 h

20: aq. NaIO₄ / methanol / 0.5 h / Ambient temperature

21: AlH₃ / tetrahydrofuran / 0.67 h / 0 °C

With pyridine; 1H-imidazole; aluminium hydride; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; n-butyllithium; Phenylselenyl chloride; cerium(III) chloride; mercury(II) perchlorate; 2-methylhexane-2-thiol; azobisisobutyronitrile; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triphenylphosphine; magnesium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; acetone; toluene; acetonitrile; benzene;

DOI:10.1248/cpb.44.515

upstream raw materials:

8-oxo-3-epischelhammeridine

16,17-methylenedioxy-3,8-dioxo-Δ¹-cis-homoerythrinan

C₁₉H₂₁NO₄

C₂₅H₂₅NO₄Se