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

Base Information

Chemical Name:2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester
CAS No.:310904-06-4
Molecular Formula:C₁₈H₂₅BrN₂O₆
Molecular Weight:445.31
Hs Code.:

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

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

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

There total 16 articles about 2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl 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:

: 146515-59-5
3-(4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione

: 310904-06-4
2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 89.2 percent / Br₂ / CCl₄; CH₂Cl₂ / 1 h / 0 °C

7: LiAl(OtBu)3H / tetrahydrofuran / 1 h / 0 °C

With dmap; hydrogen; bromine; titanium tetrachloride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 2: Baeyer-Villiger oxidation;
DOI:10.1248/cpb.48.1549

Reference yield:

: 221146-79-8
3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione

: 310904-06-4
2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91.2 percent / K₂CO₃ / dimethylformamide / 24 h / 80 °C

2: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 43 h / 20 °C

3: 93.3 percent / H₂ / 20 percent Pd(OH)2/C / ethanol / 1 h / 760 Torr

4: 89.2 percent / Br₂ / CCl₄; CH₂Cl₂ / 1 h / 0 °C

5: LiAl(OtBu)3H / tetrahydrofuran / 1 h / 0 °C

With dmap; hydrogen; bromine; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.48.1549

Reference yield:

: 221146-78-7
3-(3-formyl-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione

: 310904-06-4
2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / m-CPBA; TFA / CH₂Cl₂ / 8 h / 20 °C

2: 91.2 percent / K₂CO₃ / dimethylformamide / 24 h / 80 °C

3: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 43 h / 20 °C

4: 93.3 percent / H₂ / 20 percent Pd(OH)2/C / ethanol / 1 h / 760 Torr

5: 89.2 percent / Br₂ / CCl₄; CH₂Cl₂ / 1 h / 0 °C

6: LiAl(OtBu)3H / tetrahydrofuran / 1 h / 0 °C

With dmap; hydrogen; bromine; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Baeyer-Villiger oxidation;
DOI:10.1248/cpb.48.1549