(S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate

Base Information

• Chemical Name: (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate
• CAS No.: 1007121-07-4
• Molecular Formula: C₁₅H₁₉FO₄
• Molecular Weight: 282.312
• Mol file: 1007121-07-4.mol

Synonyms:(S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate

Chemical Property of (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate

There total 4 articles about (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate 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: 90.0%

2-benzyl-malonic acid tert-butyl ester methyl ester (4491-46-7) → (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate (1007121-07-4)

Guidance literature:

With zinc diacetate; N-fluorobis(benzenesulfon)imide; (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline); 4 A molecular sieve; In dichloromethane; for 15h; Heating;

DOI:10.1002/anie.200704093

Reference yield:

mono-tert-butyl malonate (40052-13-9) → (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate (1007121-07-4) + (R)-1-tert-butyl 3-methyl 2-fluoro-2-benzylmalonate (1277102-72-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

3: N-fluorobis(benzenesulfon)imide; silver perchlorate; C₃₀H₄₀Br₂ClFeN₂O₂ / acetonitrile / 0 - 20 °C / Inert atmosphere; Molecular sieve

With C₃₀H₄₀Br₂ClFeN₂O₂; silver perchlorate; sodium hydride; N-fluorobis(benzenesulfon)imide; triethylamine; In tetrahydrofuran; acetonitrile; mineral oil;

DOI:10.1039/c4cc01631a

Reference yield:

2-benzyl-malonic acid tert-butyl ester methyl ester (4491-46-7) → (S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate (1007121-07-4) + (R)-1-tert-butyl 3-methyl 2-fluoro-2-benzylmalonate (1277102-72-3)

Guidance literature:

With C₃₀H₄₀Br₂ClFeN₂O₂; silver perchlorate; N-fluorobis(benzenesulfon)imide; In acetonitrile; at 0 - 20 ℃; Overall yield = 72%; Overall yield = 40.7 mg; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/c4cc01631a

upstream raw materials:

2-benzyl-malonic acid tert-butyl ester methyl ester

methyl t-butyl malonate

mono-tert-butyl malonate

Downstream raw materials:

(S)-tert-butyl 2-fluoro-2-(hydroxymethyl)-3-phenylpropionate

(S)-tert-butyl 2-fluoro-2-benzylamido-3-phenylpropanoate

Refernces

• 1、 Reddy, Dhande Sudhakar,Shibata, Norio,Nagai, Jun,Nakamura, Shuichi,Toru, Takeshi,Kanemasa, Shuji. "Desymmetrization-like catalytic enantioselective fluorination of malonates and its application to pharmaceutically attractive molecules". . p. 164 - 168. Retrieved 2008/09/19.