(S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde

Base Information

• Chemical Name: (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde
• CAS No.: 214057-87-1
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396
• Mol file: 214057-87-1.mol

Synonyms:(S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde

Chemical Property of (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde

There total 11 articles about (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde 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%

1-[(S)-1-Hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-1-aza-spiro[4.5]decane-2,8-dione (214058-01-2) → (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde (214057-87-1)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1021/jo981292d

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde (214057-87-1)

Guidance literature:

Multi-step reaction with 8 steps

1: ethanol / 12 h / 25 °C

2: 2) H₂ / 2) Pd/C / 1) toluene, reflux, 4 h, 2) AcOH, 45 psi, 24 h

3: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h

4: 99 percent / NaI / acetone / Heating

5: 97 percent / Bu₃SnH, AIBN / toluene / Heating

6: LiBH₄ / diethyl ether; tetrahydrofuran

7: aq. HCl, AcOH

8: 82 percent / Dess-Martin reagent

With hydrogenchloride; dmap; lithium borohydride; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; Dess-Martin periodane; acetic acid; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; toluene;

DOI:10.1021/jo981292d

Reference yield:

2-hydroxy-3-(4-methoxyphenyl)acrylic acid (68383-86-8) → (S)-2-(2,8-Dioxo-1-aza-spiro[4.5]dec-1-yl)-3-(4-methoxy-phenyl)-propionaldehyde (214057-87-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 50 percent / NH₂OH*HCl, TsOH

2: 69 percent / BH₃*NMe₃, HCl / ethanol

3: ethanol / 12 h / 25 °C

4: 2) H₂ / 2) Pd/C / 1) toluene, reflux, 4 h, 2) AcOH, 45 psi, 24 h

5: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h

6: 99 percent / NaI / acetone / Heating

7: 97 percent / Bu₃SnH, AIBN / toluene / Heating

8: LiBH₄ / diethyl ether; tetrahydrofuran

9: aq. HCl, AcOH

10: 82 percent / Dess-Martin reagent

With hydrogenchloride; dmap; lithium borohydride; 2,2'-azobis(isobutyronitrile); trimethylamine-borane; hydroxylamine hydrochloride; hydrogen; tri-n-butyl-tin hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; toluene;

DOI:10.1021/jo981292d

upstream raw materials:

1-[(S)-1-Hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-1-aza-spiro[4.5]decane-2,8-dione

cyclohexanedione monoethylene ketal

2-hydroxy-3-(4-methoxyphenyl)acrylic acid

2-Hydroxyamino-3-(4-methoxy-phenyl)-propionic acid ethyl ester