(4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester

Base Information

• Chemical Name: (4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester
• CAS No.: 98761-64-9
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 98761-64-9.mol

Synonyms:(4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester

Chemical Property of (4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester

There total 15 articles about (4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl 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: 82.0%

benzyl chloroformate (501-53-1,94274-21-2) + (4aα,5α,8aα)-decahydroquinoline-5-carboxylic acid hydrochloride (77823-96-2,77833-73-9,98761-61-6,98761-63-8) → (4aα,5α,8aα)-1-(benzyloxycarbonyl)decahydroquinoline-5-carboxylic acid (77823-92-8,98761-60-5,98761-64-9)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Ambient temperature;

DOI:10.1021/jm00139a005

Reference yield: 73.2%

phenylmethyl (4aα,5α,8aβ)-5-formyloctahydro-1(2H)-quinolinecarboxylate (98761-69-4) → (4aα,5α,8aβ)-octahydro-1,5(2H)-quinolinedicarboxylic acid 1-phenylmethyl ester (98761-64-9)

Guidance literature:

With jones reagent; In acetone; for 0.5h;

DOI:10.1021/jm00151a001

Reference yield:

methyl (E)-6-chlorohex-2-enoate (75424-56-5) → (4aα,5α,8aα)-1-(benzyloxycarbonyl)decahydroquinoline-5-carboxylic acid (77823-92-8,98761-60-5,98761-64-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / NaI / dimethylformamide / 70 - 80 °C

2: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 1.5 h

3: 4-tert-butylcatechol, bis(trimethylsilyl)acetamide / toluene / 14 h / 200 - 210 °C

4: 91 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 2068.6 Torr / Ambient temperature

5: 83 percent / 4percent aq. NaOH / 1.5 h / Heating

6: 80 percent / conc. HCl / 5 h / Heating

7: 82 percent / K₂CO₃ / acetone / 4 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; 4-tert-Butylcatechol; hydrogen; sodium hydride; potassium carbonate; bis-(trimethylsilyl)acetamide; sodium iodide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm00139a005

upstream raw materials:

benzyl chloroformate

(4aα,5α,8aα)-decahydroquinoline-5-carboxylic acid hydrochloride

(E)-6-Iod-2-hexensaeure-methylester

methyl (E)-6-chlorohex-2-enoate

Refernces

• 1、 Witiak,Tomita,Patch,Enna. "Epimeric cis-decahydroquinoline-5-carboxylic acids: Effects on γ-aminobutyric acid uptake and receptor binding in vitro". . p. 788 - 794. Retrieved 2007/10/02.