Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester

Base Information

• Chemical Name: Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester
• CAS No.: 57907-27-4
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• Mol file: 57907-27-4.mol

Synonyms:

Chemical Property of Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester

There total 10 articles about Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl 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: 70.2%

acetic anhydride (108-24-7) + (±)-lasubine II (89771-49-3) → Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester (57907-27-4,60352-71-8,80324-17-0)

Guidance literature:

In pyridine; for 15h; Ambient temperature;

Reference yield:

N-hydroxypiperidine (4801-58-5) → Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester (57907-27-4,60352-71-8,80324-17-0)

Guidance literature:

Multi-step reaction with 8 steps

1: yellow HgO / CH₂Cl₂ / 1.5 h / -10 - 0 °C

2: toluene / 2 h / Heating

3: 1.) methanesulfonyl chloride, 2.) 50percent AcOH, Zn / 1.) pyridine, r.t. 2.5 h, 2.) H₂O, r.t. 2.5 h

4: 93.4 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

5: 91.8 percent / NaOMe, MeOH / 10.5 h / Ambient temperature

6: 77.8 percent / H₂ / 10percent Pd-C / methanol / 38 h / 760 Torr / Ambient temperature

7: 87.3 percent / methanol / 15 h / 0 °C

8: 70.2 percent / pyridine / 15 h / Ambient temperature

With methanol; hydrogen; sodium methylate; acetic acid; methanesulfonyl chloride; triphenylphosphine; mercury(II) oxide; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; toluene;

Reference yield:

2,3,4,5-tetrahydropyridine N-oxide (34418-91-2) → Acetic acid (2R,4R,9aR)-4-(3,4-dimethoxy-phenyl)-octahydro-quinolizin-2-yl ester (57907-27-4,60352-71-8,80324-17-0)

Guidance literature:

Multi-step reaction with 7 steps

1: toluene / 2 h / Heating

2: 1.) methanesulfonyl chloride, 2.) 50percent AcOH, Zn / 1.) pyridine, r.t. 2.5 h, 2.) H₂O, r.t. 2.5 h

3: 93.4 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

4: 91.8 percent / NaOMe, MeOH / 10.5 h / Ambient temperature

5: 77.8 percent / H₂ / 10percent Pd-C / methanol / 38 h / 760 Torr / Ambient temperature

6: 87.3 percent / methanol / 15 h / 0 °C

7: 70.2 percent / pyridine / 15 h / Ambient temperature

With methanol; hydrogen; sodium methylate; acetic acid; methanesulfonyl chloride; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; toluene;

upstream raw materials:

acetic anhydride

(±)-lasubine II

N-hydroxypiperidine

2,3,4,5-tetrahydropyridine N-oxide