(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Base Information

• Chemical Name: (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine
• CAS No.: 271260-96-9
• Molecular Formula: C₂₁H₃₃NO₃
• Molecular Weight: 347.498
• Mol file: 271260-96-9.mol

Synonyms:(R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Chemical Property of (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine

There total 5 articles about (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine 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: 77.0%

2,4,6-trimethylphenyl bromide (576-83-0) + tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (115378-31-9) → (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine (271260-96-9)

Guidance literature:

tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate; With 9-borabicyclo[3.3.1]nonane dimer; In toluene; at 80 - 85 ℃;

2,4,6-trimethylphenyl bromide; With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In toluene; at 90 ℃; Further stages.;

DOI:10.1021/ol005645i

Reference yield: 69.0%

2,4,6-trimethylphenyl bromide (576-83-0) + (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) + diazomethyl-trimethyl-silane (18107-18-1) → (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine (271260-96-9)

Guidance literature:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; diazomethyl-trimethyl-silane; With triphenylphosphine; isopropyl alcohol; copper(l) chloride; In tetrahydrofuran; at 60 ℃;

With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; toluene; at 80 ℃;

2,4,6-trimethylphenyl bromide; With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; toluene; at 90 ℃; Further stages.;

DOI:10.1021/ja0733235

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine (271260-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2.1 g / NaHCO₃ / methanol; ethyl acetate; H₂O / biphasic

2.1: 46 percent / Pseudomonas cepecia (Amano PS-30) lipase / CH₂Cl₂ / 20 °C / Enzymatic reaction

3.1: BF₃*Et₂O / acetone / -20 - 20 °C

4.1: 9-BBN / toluene / 80 - 85 °C

4.2: 77 percent / aq. NaOH; Pd(PPh₃)4; TBAI / toluene / 90 °C

With 9-borabicyclo[3.3.1]nonane dimer; Pseudomonas cepecia (Amano PS-30) lipase; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In methanol; dichloromethane; water; ethyl acetate; acetone; toluene; 1.1: Acylation / 2.1: Acetylation / 3.1: Condensation / 4.1: hydroboration / 4.2: Suzuki cross-coupling;

DOI:10.1021/ol005645i

upstream raw materials:

2,4,6-trimethylphenyl bromide

tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate

di-tert-butyl dicarbonate

(R)-2-(N-tert-butoxycarbonylamino)-3-buten-1-ol

Refernces

• 1、 Sabat, Mark,Johnson, Carl R.. "Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives". . p. 1089 - 1091. Retrieved 2007/10/03.