3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione

Base Information

• Chemical Name: 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione
• CAS No.: 221146-80-1
• Molecular Formula: C₁₈H₂₄N₂O₆
• Molecular Weight: 364.398
• Mol file: 221146-80-1.mol

Synonyms:3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione

Chemical Property of 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione

There total 9 articles about 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione 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: 93.3%

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione (310903-98-1) → 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione (221146-80-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 1h; under 760 Torr;

DOI:10.1248/cpb.48.1549

Reference yield:

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione (310903-97-0) → 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione (221146-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 43 h / 20 °C

2: 93.3 percent / H₂ / 20 percent Pd(OH)2/C / ethanol / 1 h / 760 Torr

With dmap; hydrogen; triethylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1248/cpb.48.1549

Reference yield:

3-(4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione (146515-59-5) → 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxy-carbonyl-1-methyl-2,5-piperazinedione (221146-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 76.7 percent / TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

2: 75 percent / m-CPBA; TFA / CH₂Cl₂ / 8 h / 20 °C

3: 91.2 percent / K₂CO₃ / dimethylformamide / 24 h / 80 °C

4: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 43 h / 20 °C

5: 93.3 percent / H₂ / 20 percent Pd(OH)2/C / ethanol / 1 h / 760 Torr

With dmap; hydrogen; titanium tetrachloride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium dihydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide; 2: Baeyer-Villiger oxidation;

DOI:10.1248/cpb.48.1549

upstream raw materials:

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione

3-(4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione

2-bromo-5-isopropyloxy-4-methoxy-3-methylbenzaldehyde

Downstream raw materials:

2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester

3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-4-isopropyloxycarbonyl-1-methyl-2,5-piperazinedione