(+/-)-isococculidine

Base Information

• Chemical Name: (+/-)-isococculidine
• CAS No.: 78463-72-6
• Molecular Formula: C₁₈H₂₃NO₂
• Molecular Weight: 285.386
• Mol file: 78463-72-6.mol

Synonyms:

Chemical Property of (+/-)-isococculidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-isococculidine

There total 14 articles about (+/-)-isococculidine 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:

ethyl 4-methoxycyclohexanone-2-glyoxylate (66800-24-6) → (+/-)-isococculidine (60229-91-6,78463-72-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.) 85percent H₃PO₄ / 1.) benzene, reflux, 10 h; 2.) MeOH, reflux, 20 h

2: 19.84 g / NaBH₄ / methanol; H₂O / Ambient temperature

3: 10.23 g / concd. H₂SO₄ / 3 h / 40 - 50 °C

4: 54.6 percent / 20percent HCl / 20 h / Heating

5: 1.) NaNO₂, 10percent HCl; 2.) hypophosphorous acid / 1.) H₂O, 5-0 deg C; 2.) H₂O, 0 deg C, 24 h

6: 80 percent / p-toluenesulfonic acid / 1.5 h / Heating

7: 157 mg / m-chloroperbenzoic acid / CHCl₃ / 48 h / Ambient temperature

8: 1.) NaBH₄, diphenyldiselenide; 2.) 30percent H₂O₂ / 1.) EtOH, reflux, 2 h; 2.) EtOH, THF, 2 h

9: 96.4 mg / 6N HCl / 20 h / Heating

10: 102 mg / pyridine / 72 h

11: 9.5 mg / LiAlH₄ / diethyl ether / 3 h / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; phosphoric acid; sulfuric acid; diphenyl diselenide; dihydrogen peroxide; hypophosphorous acid; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; In methanol; diethyl ether; chloroform; water;

DOI:10.1248/cpb.29.396

Reference yield:

3-ethoxycarbamido-4-methoxyphenylethylamine (19712-54-0) → (+/-)-isococculidine (60229-91-6,78463-72-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.) 85percent H₃PO₄ / 1.) benzene, reflux, 10 h; 2.) MeOH, reflux, 20 h

2: 19.84 g / NaBH₄ / methanol; H₂O / Ambient temperature

3: 10.23 g / concd. H₂SO₄ / 3 h / 40 - 50 °C

4: 54.6 percent / 20percent HCl / 20 h / Heating

5: 1.) NaNO₂, 10percent HCl; 2.) hypophosphorous acid / 1.) H₂O, 5-0 deg C; 2.) H₂O, 0 deg C, 24 h

6: 80 percent / p-toluenesulfonic acid / 1.5 h / Heating

7: 157 mg / m-chloroperbenzoic acid / CHCl₃ / 48 h / Ambient temperature

8: 1.) NaBH₄, diphenyldiselenide; 2.) 30percent H₂O₂ / 1.) EtOH, reflux, 2 h; 2.) EtOH, THF, 2 h

9: 96.4 mg / 6N HCl / 20 h / Heating

10: 102 mg / pyridine / 72 h

11: 9.5 mg / LiAlH₄ / diethyl ether / 3 h / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; phosphoric acid; sulfuric acid; diphenyl diselenide; dihydrogen peroxide; hypophosphorous acid; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; In methanol; diethyl ether; chloroform; water;

DOI:10.1248/cpb.29.396

Reference yield:

15-methoxyerythrinan-8-one-2,7-oxide (78463-78-2) → (+/-)-isococculidine (60229-91-6,78463-72-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / p-toluenesulfonic acid / 1.5 h / Heating

2: 157 mg / m-chloroperbenzoic acid / CHCl₃ / 48 h / Ambient temperature

3: 1.) NaBH₄, diphenyldiselenide; 2.) 30percent H₂O₂ / 1.) EtOH, reflux, 2 h; 2.) EtOH, THF, 2 h

4: 96.4 mg / 6N HCl / 20 h / Heating

5: 102 mg / pyridine / 72 h

6: 9.5 mg / LiAlH₄ / diethyl ether / 3 h / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; diphenyl diselenide; dihydrogen peroxide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; chloroform;

DOI:10.1248/cpb.29.396

upstream raw materials:

diazomethane

isococculine

Toluene-4-sulfonic acid (2S,4aS,5S,13bR)-2,12-dimethoxy-6-oxo-2,4a,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinolin-5-yl ester

ethyl 4-methoxycyclohexanone-2-glyoxylate