rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate

Base Information

• Chemical Name: rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate
• CAS No.: 87923-01-1
• Molecular Formula: C₂₁H₃₀ClNO₂
• Molecular Weight: 363.928
• Mol file: 87923-01-1.mol

Synonyms:

Chemical Property of rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate

There total 6 articles about rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate 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: 70.0%

Isopropenyl acetate (108-22-5) + rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-ol (75384-68-8) → rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate (87923-01-1)

Guidance literature:

With toluene-4-sulfonic acid; for 1h; Heating;

DOI:10.1021/jm00368a011

Reference yield:

5-(2-chlorophenyl)-2-piperidone (87922-77-8) → rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate (87923-01-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.) aq. K₂CO₃ / 1.) CH₂Cl₂, a) reflux, 4 h, b) RT, 15 h, 2.) CH₂Cl₂, RT, 2 h

2: 54 percent / p-toluenesulfonic acid / methanol / 20 h / Ambient temperature

3: 81 percent / diisobutylaluminum hydride / 1,2-dimethoxy-ethane; toluene / 1 h / -30 - -20 °C

4: 81 percent / 6 N HCl / 3 h / Heating

5: tetrahydrofuran; pentane / 0.5 h / -75 °C

6: 70 percent / p-toluenesulfonic acid / 1 h / Heating

With hydrogenchloride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; toluene; pentane;

DOI:10.1021/jm00368a011

Reference yield:

3-(o-chlorophenyl)-6-ethoxy-2,3,4,5-tetrahydropyridine (87922-85-8) → rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-yl acetate (87923-01-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 54 percent / p-toluenesulfonic acid / methanol / 20 h / Ambient temperature

2: 81 percent / diisobutylaluminum hydride / 1,2-dimethoxy-ethane; toluene / 1 h / -30 - -20 °C

3: 81 percent / 6 N HCl / 3 h / Heating

4: tetrahydrofuran; pentane / 0.5 h / -75 °C

5: 70 percent / p-toluenesulfonic acid / 1 h / Heating

With hydrogenchloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; toluene; pentane;

DOI:10.1021/jm00368a011

upstream raw materials:

Isopropenyl acetate

rac-(9aβH)-2α-tert-butyl-7β-(2-chlorophenyl)octahydro-2H-quinolizin-2-ol

5-(2-chlorophenyl)-2-piperidone

3-(o-chlorophenyl)-6-ethoxy-2,3,4,5-tetrahydropyridine

Refernces