1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester

Base Information

• Chemical Name: 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester
• CAS No.: 89681-01-6
• Molecular Formula: C₃₁H₄₁NO₈
• Molecular Weight: 555.668
• Mol file: 89681-01-6.mol

Synonyms:

Chemical Property of 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester

There total 46 articles about 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl 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-(α,α-ethyleenedithioethyl)pyridine (52155-97-2) → 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester (89681-01-6,107343-24-8,107343-27-1)

Guidance literature:

Multi-step reaction with 9 steps

1: potassium ferricyanide, KOH

2: H₂ / Raney Ni W-2 / ethanol / Ambient temperature; room temperature, 1 h then 35 degC, 12 h

3: 95 percent / 10percent HCl / H₂O / 2 h / Heating

4: 84 percent / hydrazine hydrate, KOH / H₂O; ethane-1,2-diol / 120 degC, 1 h then 190-195 degC, 3 h

5: 96 percent / K₂CO₃ / acetone / 24 h / Heating

6: 94 percent / diisopropylamine, n-butyllithium, hexamethylphosphoramide / tetrahydrofuran; hexane / 2 h / -78 °C

7: sodium metaperiodate / methanol; H₂O / 18 h / Ambient temperature

8: CaCO₃ / toluene / 1 h / Heating

9: NaOEt / ethanol / 70 degC, 2 h, reflux, 6 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium periodate; n-butyllithium; hydrogen; sodium ethanolate; potassium carbonate; hydrazine hydrate; diisopropylamine; calcium carbonate; potassium hexacyanoferrate(III); Raney Ni W-2; In tetrahydrofuran; methanol; ethanol; hexane; water; ethylene glycol; acetone; toluene;

DOI:10.1248/cpb.33.5316

Reference yield:

3-(α,α-ethyleenedithioethyl)pyridine (52155-97-2) → 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester (89681-01-6,107343-24-8,107343-27-1)

Guidance literature:

Multi-step reaction with 9 steps

1: potassium ferricyanide, KOH

2: H₂ / Raney Ni W-2 / ethanol / Ambient temperature; room temperature, 1 h then 35 degC, 12 h

3: 95 percent / 10percent HCl / H₂O / 2 h / Heating

4: 84 percent / hydrazine hydrate, KOH / H₂O; ethane-1,2-diol / 120 degC, 1 h then 190-195 degC, 3 h

5: 96 percent / K₂CO₃ / acetone / 24 h / Heating

6: 94 percent / diisopropylamine, n-butyllithium, hexamethylphosphoramide / tetrahydrofuran; hexane / 2 h / -78 °C

7: sodium metaperiodate / methanol; H₂O / 18 h / Ambient temperature

8: CaCO₃ / toluene / 1 h / Heating

9: NaOEt / ethanol / 70 degC, 2 h, reflux, 6 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium periodate; n-butyllithium; hydrogen; sodium ethanolate; potassium carbonate; hydrazine hydrate; diisopropylamine; calcium carbonate; potassium hexacyanoferrate(III); Raney Ni W-2; In tetrahydrofuran; methanol; ethanol; hexane; water; ethylene glycol; acetone; toluene;

DOI:10.1248/cpb.33.5316

Reference yield:

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (55676-25-0) → 1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid diethyl ester (89681-01-6,107343-24-8,107343-27-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / benzene / 5 h / Ambient temperature

2: 1.) H₂; 2.) NaBH₄ / 1.) Adams catalyst / 1.) ethanol/water, 18 h, room temperature; 2.) ethanol/water, room temperature

3: 98 percent / 1N HCl / H₂O / 2 h / 40 °C

4: 82 percent / Hg(OAc)2-EDTA / aq. acetic acid / Heating

5: 89 percent / H₂, 70percent HClO₄ / 10percent Pd-C / ethanol; H₂O / 6 h / Ambient temperature

6: 84 percent / hydrazine hydrate, KOH / H₂O; ethane-1,2-diol / 120 degC, 1 h then 190-195 degC, 3 h

7: 96 percent / K₂CO₃ / acetone / 24 h / Heating

8: 94 percent / diisopropylamine, n-butyllithium, hexamethylphosphoramide / tetrahydrofuran; hexane / 2 h / -78 °C

9: sodium metaperiodate / methanol; H₂O / 18 h / Ambient temperature

10: CaCO₃ / toluene / 1 h / Heating

11: NaOEt / ethanol / 70 degC, 2 h, reflux, 6 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; perchloric acid; Hg(OAc)2*EDTA; hydrogen; sodium ethanolate; potassium carbonate; hydrazine hydrate; diisopropylamine; calcium carbonate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; water; ethylene glycol; acetic acid; acetone; toluene; benzene;

DOI:10.1248/cpb.33.5316

upstream raw materials:

1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-5,6-dihydro-2(1H)-pyridinone

diethyl malonate

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

3-(α,α-ethyleenedithioethyl)pyridine

Refernces