(±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone

Base Information

• Chemical Name: (±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone
• CAS No.: 1614264-84-4
• Molecular Formula: C₁₇H₂₀BrNO₃
• Molecular Weight: 366.255
• Mol file: 1614264-84-4.mol

Synonyms:(±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone

Chemical Property of (±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone

There total 1 articles about (±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone 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: 88.0%

cycl-isopropylidene malonate (2033-24-1) + tert-butyl acetoacetate (1694-31-1) + 4-bromo-benzaldehyde (1122-91-4) → (±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone (1614264-84-4)

Guidance literature:

With ammonium acetate; acetic acid; at 80 ℃; for 4h; Reflux;

DOI:10.1016/j.tet.2014.05.012

Reference yield: 74.0%

(±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone (1614264-84-4) → (±)-4-(4-bromophenyl)-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone (1614264-77-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tet.2014.05.012

Reference yield:

(±)-4-(4-bromophenyl)-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridone (1614264-84-4) → methyl 4-(4-bromophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate (1334529-05-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / dichloromethane / 0 °C

2.1: caesium carbonate / N,N-dimethyl-formamide

2.2: 24 h / 20 °C

3.1: water; Candida antarctica lipase B / tert-butyl methyl ether / 11 h / 28 °C / Enzymatic reaction

4.1: water; Candida antarctica lipase B / tert-butyl methyl ether / 2.5 h / 28 °C / Enzymatic reaction

5.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h

5.2: 4 h / 20 °C

With Candida antarctica lipase B; water; caesium carbonate; trifluoroacetic acid; In dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2014.05.012

upstream raw materials:

cycl-isopropylidene malonate

tert-butyl acetoacetate

4-bromo-benzaldehyde

Downstream raw materials:

(±)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone

(S)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone

C₁₃H₁₂BrNO₃

(R)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone