(4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid

Base Information

• Chemical Name: (4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid
• CAS No.: 57103-66-9
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.551
• Mol file: 57103-66-9.mol

Synonyms:(4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid

Chemical Property of (4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid

There total 35 articles about (4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid 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:

{(4S,5R)-1-[2-(2-Benzyloxy-3,4-dimethoxy-phenyl)-ethyl]-5-ethyl-2-oxo-piperidin-4-yl}-acetic acid ethyl ester (57130-37-7) → (4S,5R)-(-)-1-(2-(2-Benzyloxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid (57103-66-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 40 ℃; for 10h; Yield given;

DOI:10.1021/jo01298a025

Reference yield:

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (55676-25-0) → (+/-)-trans-1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid (57103-66-9,57103-67-0,89709-06-8)

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

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; 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

Reference yield:

3-(α,α-ethyleenedithioethyl)pyridine (52155-97-2) → (+/-)-trans-1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid (57103-66-9,57103-67-0,89709-06-8)

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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium periodate; n-butyllithium; hydrogen; 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

upstream raw materials:

{(4S,5R)-1-[2-(2-Benzyloxy-3,4-dimethoxy-phenyl)-ethyl]-5-ethyl-2-oxo-piperidin-4-yl}-acetic acid ethyl ester

(4R,5R)-(+)-1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid

2-(benzyloxy)-3,4-dimethoxyphenacyl bromide

benzyl bromide

Downstream raw materials:

(4R,5R)-(+)-1-(2-benzyloxy-3,4-dimethoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid

{(R)-1-[2-(2-Benzyloxy-3,4-dimethoxy-phenyl)-ethyl]-5-ethyl-2-oxo-piperidin-4-yl}-acetic acid

(4R,5R)-(+)-1-(2-(2-Hydroxy-3,4-dimethoxyphenyl)-ethyl)-5-ethyl-2-oxo-4-piperidineacetic Acid

{(R)-5-Ethyl-1-[2-(2-hydroxy-3,4-dimethoxy-phenyl)-ethyl]-2-oxo-piperidin-4-yl}-acetic acid