(+/-)-CI-CDPI₁

Base Information

• Chemical Name: (+/-)-CI-CDPI₁
• CAS No.: 119907-66-3
• Molecular Formula: C₂₁H₁₈N₄O₃
• Molecular Weight: 374.399
• Mol file: 119907-66-3.mol

Synonyms:

Chemical Property of (+/-)-CI-CDPI₁

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-CI-CDPI₁

There total 11 articles about (+/-)-CI-CDPI₁ 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: 90.0%

seco-CI-CDPI1 (119880-08-9) → (+/-)-CI-CDPI1 (119907-66-3,128050-92-0,128050-93-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 24 ℃; for 0.416667h;

Reference yield:

3-(benzyloxy)aniline (1484-26-0) → (+/-)-CI-CDPI1 (119907-66-3,128050-92-0,128050-93-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 42 percent / N-bromosuccinimide, H₂SO₄ / tetrahydrofuran / 10 h / -78 °C

2: 85 percent / dioxane / 10 h / 105 °C

3: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C

4: 91 percent / Bu₃SnH, AIBN / benzene / 3 h / 80 °C

5: 1.) ozone, 2.) NaBH₄ / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H₂O, -78 to 24 deg C, 4 h

6: 89 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

7: 75 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr

8: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C

9: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, Et₃N / dimethylformamide / 45 h / 24 °C

10: 90 percent / NaH / tetrahydrofuran / 0.42 h / 24 °C

With hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00267a004

Reference yield:

5-(Benzyloxy)-2-bromophenylamine (119879-90-2) → (+/-)-CI-CDPI1 (119907-66-3,128050-92-0,128050-93-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / dioxane / 10 h / 105 °C

2: 68 percent / NaH / tetrahydrofuran; dimethylformamide / 3 h / 25 °C

3: 91 percent / Bu₃SnH, AIBN / benzene / 3 h / 80 °C

4: 1.) ozone, 2.) NaBH₄ / 1.) EtOH, -78 deg C, 3 min, 2.) EtOH, H₂O, -78 to 24 deg C, 4 h

5: 89 percent / Et₃N / CH₂Cl₂ / 0.42 h / 0 °C

6: 75 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 7 h / 24 °C / 760 Torr

7: 100 percent / HCl / ethyl acetate / 0.17 h / 24 °C

8: 84 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide, Et₃N / dimethylformamide / 45 h / 24 °C

9: 90 percent / NaH / tetrahydrofuran / 0.42 h / 24 °C

With hydrogenchloride; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00267a004

upstream raw materials:

seco-CI-CDPI₁

3-(benzyloxy)aniline

5-(Benzyloxy)-2-bromophenylamine

5-(benzyloxy)-2-bromo-N-((tert-butyloxy)carbonyl)aniline

Refernces

• 1、 Boger,Wysocki Jr.. "Total synthesis of (±)-N-(phenylsulfonyl)- and (±)-N-(tert-butyloxycarbonyl)-CI, (±)-CI-CDPI1, and (±)-CI-CDPI2: CC-1065 functional analogues incorporating the parent 1,2,7,7a-tetrahydrocycloprop[1,2-c]indol-4-one (CI) left-hand subu". . p. 1238 - 1240. Retrieved 2007/10/02.