C₂₇H₂₁NO₅

Base Information

• Chemical Name: C₂₇H₂₁NO₅
• CAS No.: 135106-79-5
• Molecular Formula: C₂₇H₂₁NO₅
• Molecular Weight: 439.467
• Mol file: 135106-79-5.mol

Synonyms:

Chemical Property of C₂₇H₂₁NO₅

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₇H₂₁NO₅

There total 17 articles about C₂₇H₂₁NO₅ 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:

3-(benzyloxy)-7,8,9,10-tetrahydrophenanthridine (144019-65-8) → C27H21NO5 (135106-79-5,141395-31-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

2: 80 percent / 14 h / 25 °C

3: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

4: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

5: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

6: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

7: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

8: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

9: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

10: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

11: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

12: 59 percent / sat. aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 1 h / 25 °C

13: 42 percent / LDA / toluene; cyclohexane / 0.33 h / -78 °C

14: Cs₂CO₃, 18-crown-6 / acetonitrile / 25 °C

15: Irradiation

With 2,6-dimethylpyridine; propylamine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; hydrogen bromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; toluene; acetonitrile;

DOI:10.1021/ja00049a023

Reference yield:

N-(3-hydroxyphenyl)-1,4-dioxaspiro<4.5>decane-6-carboxamide (144019-57-8) → C27H21NO5 (135106-79-5,141395-31-5)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

2: 1.) 37percent aq. HCl, 2.) DIBAL, LiAlH₄, 3.) silica gel, O₂

3: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

4: 80 percent / 14 h / 25 °C

5: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

7: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

8: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

9: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

10: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

11: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

12: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

13: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

14: 59 percent / sat. aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 1 h / 25 °C

15: 42 percent / LDA / toluene; cyclohexane / 0.33 h / -78 °C

16: Cs₂CO₃, 18-crown-6 / acetonitrile / 25 °C

17: Irradiation

With 2,6-dimethylpyridine; hydrogenchloride; propylamine; potassium cyanide; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; hydrogen bromide; hydrogen; oxygen; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; toluene; acetonitrile;

DOI:10.1021/ja00049a023

Reference yield:

3-(benzyloxy)-7,8,9,10-tetrahydrophenanthridine N-oxide (144019-66-9) → C27H21NO5 (135106-79-5,141395-31-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 80 percent / 14 h / 25 °C

2: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

3: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

4: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

5: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

6: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

7: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

8: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

9: 82 percent / 48percent aq. HBr / tetrahydrofuran / 2 h / 25 °C

10: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

11: 59 percent / sat. aq. NaHCO₃, m-CPBA / CH₂Cl₂ / 1 h / 25 °C

12: 42 percent / LDA / toluene; cyclohexane / 0.33 h / -78 °C

13: Cs₂CO₃, 18-crown-6 / acetonitrile / 25 °C

14: Irradiation

With 2,6-dimethylpyridine; propylamine; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; hydrogen bromide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; silver nitrate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; toluene; acetonitrile;

DOI:10.1021/ja00049a023

upstream raw materials:

C₃₃H₂₄N₂O₇

3-(benzyloxy)-7,8,9,10-tetrahydrophenanthridine

N-(3-hydroxyphenyl)-1,4-dioxaspiro<4.5>decane-6-carboxamide

3-(benzyloxy)-7,8,9,10-tetrahydrophenanthridine N-oxide

Downstream raw materials:

C₂₀H₁₇NO₄

C₂₇H₂₁NO₆