4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 186366-90-5
• Molecular Formula: C₁₇H₂₄BrNO₃
• Molecular Weight: 370.286
• Mol file: 186366-90-5.mol

Synonyms:4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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: 98.0%

2,2-dimethoxy-propane (77-76-9) + [2-(2-Bromo-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester → 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (186366-90-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jm960582o

Reference yield: 87.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (186366-90-5) → 4-(2-Formyl-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (186366-91-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

DOI:10.1021/jm960582o

Reference yield:

4-(2-Bromo-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (186366-90-5) → 2-{6-[2-(3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-ylmethyl)-phenyl]-hexyl}-malonic acid monomethyl ester (186366-96-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

2: 80 percent / t-BuOK / CH₂Cl₂ / 1 h / Ambient temperature

3: 6.9 g / LiAlH₄ / 1 h

4: 6.3 g / pyridinium chlorochromate / CH₂Cl₂ / 0.5 h

5: 4.3 g / piperidine, benzoic acid / toluene / 6 h / Heating

6: 3.62 g / H₂ / 10percent Pd/C / ethyl acetate / 17 h / 2585.7 Torr

With piperidine; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; hydrogen; benzoic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm960582o

upstream raw materials:

2,2-dimethoxy-propane

Downstream raw materials:

4-(2-Formyl-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

2-{5-[2-(2-Amino-3-hydroxy-propyl)-phenyl]-pentyl}-malonic acid monomethyl ester

{6-[2-(2-amino-3-hydroxypropyl)phenyl]hexyl}propanedioic acid 1-methyl ester

2-{7-[2-(2-Amino-3-hydroxy-propyl)-phenyl]-heptyl}-malonic acid monomethyl ester