(+/-)-schelhammericine

Base Information

• Chemical Name: (+/-)-schelhammericine
• CAS No.: 102487-78-5
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• Mol file: 102487-78-5.mol

Synonyms:

Chemical Property of (+/-)-schelhammericine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-schelhammericine

There total 50 articles about (+/-)-schelhammericine 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: 98.0%

(+/-)-8-oxo-schelhemmericine (102487-83-2,102487-84-3) → (+/-)-schelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.3574

Reference yield: 94.0%

(+/-)-8-oxo-epischelhemmericine (102487-83-2,102487-84-3) → (+/-)-epischelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.3574

Reference yield:

7α-hydroxy-6β-methoxycarbonyl-16,17-methylenedioxy-2,8-dioxo-Δ3-homoerithrinan (89412-91-9) → (+/-)-epischelhammericine (21030-78-4,24204-36-2,102487-78-5,102487-79-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / H₂ / 5percent Pd/C / acetone / 6.5 h / Ambient temperature

2: 97 percent / pyridine / 12 h / Ambient temperature

3: 62 percent / DBU / toluene / 2 h / Heating

4: 1.) PhSeCl, BF₃*Et₂O, 2.) MPC / 1.) THF, reflux, 10.5 h 2.) 13 h, RT

5: 96 percent / NaBH₄ / methanol; tetrahydrofuran / 0.75 h / Ambient temperature

6: 1.) NaH, imidazole / 1.) THF, reflux, 3h 2.) 30 min

7: 67 percent / 1.) Bu3SnH, α,α-bisisobutyronitrile 2.) HCl / 1.)toluene, reflux, 5h 2.) 50 deg C, 2.5 h

8: 62 percent / CaCl₂, 3-ethylpentane-3-thiol / dimethylsulfoxide / 1 h / 140 - 145 °C

9: 13 percent / Bu₄NBH₄ / methanol / 1.17 h / 0 °C

10: 1.) NaH, imidazole 2.) Bu₄NHSO₄ / 1.) THF, reflux, 1h 2.) RT, 5h

11: 94 percent / LiAlH₄, AlCl₃ / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); 3-ethylpentan-3-yl thiol; boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; myristyl-gamma-picolinium chloride; sodium hydride; tetrabutylammonium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide; acetone; toluene;

DOI:10.1248/cpb.44.500

upstream raw materials:

(+/-)-8-oxo-epischelhemmericine

2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-2-benzodiazepine-1-thione

methyl 2-(2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-2-benzazepin-1-ylidene)acetate

C₁₈H₁₇NO₄