apovincaminic acid methyl mandelate ester

Base Information

• Chemical Name: apovincaminic acid methyl mandelate ester
• CAS No.: 95407-52-6
• Molecular Formula: C₂₉H₃₀N₂O₄
• Molecular Weight: 470.568
• Mol file: 95407-52-6.mol

Synonyms:

Chemical Property of apovincaminic acid methyl mandelate ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of apovincaminic acid methyl mandelate ester

There total 15 articles about apovincaminic acid methyl mandelate ester 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-(2-bromoethyl)-1H-indole (3389-21-7) → apovincaminic acid methyl mandelate ester (95407-52-6,95420-14-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / NaHCO₃ / acetonitrile / 24 h / Heating

2: H₂ / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr

3: 1.) pyridine, TsCl, 2.) NaHCO₃ / 1.) CH₂Cl₂, 1 h, 2.) 1 h

4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h

5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h

6: 90 percent / NaBH₄ / methanol / 0.05 h / -25 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 55 percent / DBU / 1 h / 100 °C

9: aq. NaOH / methanol; tetrahydrofuran / 12 h

10: pyridine, TsCl / 1 h / 0 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a017

Reference yield:

1-phenylpropyl (2S,3R)-3-cyano-3-ethylpipecolate (95407-25-3,95407-56-0) → apovincaminic acid methyl mandelate ester (95407-52-6,95420-14-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / NaHCO₃ / acetonitrile / 24 h / Heating

2: H₂ / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr

3: 1.) pyridine, TsCl, 2.) NaHCO₃ / 1.) CH₂Cl₂, 1 h, 2.) 1 h

4: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h

5: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h

6: 90 percent / NaBH₄ / methanol / 0.05 h / -25 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 55 percent / DBU / 1 h / 100 °C

9: aq. NaOH / methanol; tetrahydrofuran / 12 h

10: pyridine, TsCl / 1 h / 0 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a017

Reference yield:

N-(3-chloropropyl)-N-(9-phenylfluorenyl)-3-cyanoalanine benzyl ester (95407-43-5) → apovincaminic acid methyl mandelate ester (95407-52-6,95420-14-7)

Guidance literature:

Multi-step reaction with 12 steps

1: NaI / acetonitrile / 22 h / Heating

3: 80 percent / NaHCO₃ / acetonitrile / 24 h / Heating

4: H₂ / 10percent Pd/C / methanol; ethyl acetate / 4 h / 2585.7 Torr

5: 1.) pyridine, TsCl, 2.) NaHCO₃ / 1.) CH₂Cl₂, 1 h, 2.) 1 h

6: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) - 30 deg C, 1 h

7: 56 percent / LDA / tetrahydrofuran; hexane / 1.0 -78 deg C, 15 min, 2.) 0 deg C, 9 h

8: 90 percent / NaBH₄ / methanol / 0.05 h / -25 °C

9: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

10: 55 percent / DBU / 1 h / 100 °C

11: aq. NaOH / methanol; tetrahydrofuran / 12 h

12: pyridine, TsCl / 1 h / 0 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jo00208a017

upstream raw materials:

(RS)-methyl mandelate

Apovincaminic acid

3-(2-bromoethyl)-1H-indole

1-phenylpropyl (2S,3R)-3-cyano-3-ethylpipecolate

Refernces