(R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate
• CAS No.: 1039826-29-3
• Molecular Formula: C₁₀H₁₈BrNO₂
• Molecular Weight: 264.162
• Hs Code.: 2933990090
• Mol file: 1039826-29-3.mol

Synonyms:2-(Bromomethyl)pyrrolidine-1-carboxylic acid (R)-tert-butyl ester;tert-Butyl (2R)-2-(bromomethyl)pyrrolidine-1-carboxylate;

Chemical Property of (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 300.053 °C at 760 mmHg
• Flash Point: 135.268 °C
• PSA: 29.54000
• Density: 1.313 g/cm³
• LogP: 2.71870
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99% ^*data from raw suppliers

(R)-tert-butyl2-(bromomethyl)pyrrolidine-1-carboxylate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate

There total 3 articles about (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate 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: 60.0%

1-(tert-butoxycarbonyl)prolin-2R-ol (59378-81-3,69610-40-8,83435-58-9) → (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate (1039826-29-3)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 16h;

Reference yield:

(R)-1-<(1,1-dimethylethoxy)carbonyl>-2-pyrrolidinemethanolmethanesulfonate (132482-10-1) → (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate (1039826-29-3)

Guidance literature:

With lithium bromide; In acetone; Reflux;

DOI:10.1016/j.bmcl.2017.07.009

Reference yield:

N-(tert-butoxycarbonyl)-D-proline (37784-17-1,59433-50-0) → (R)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate (1039826-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: borane-THF / tetrahydrofuran / 0 °C

2: triphenylphosphine; carbon tetrabromide / dichloromethane / 20 °C

With borane-THF; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: |Appel Halogenation;

DOI:10.1021/acs.jmedchem.7b00316

upstream raw materials:

1-(tert-butoxycarbonyl)prolin-2R-ol

N-(tert-butoxycarbonyl)-D-proline

(R)-1-<(1,1-dimethylethoxy)carbonyl>-2-pyrrolidinemethanolmethanesulfonate

Refernces

• 1、 Günther, Marcel,Lategahn, Jonas,Juchum, Michael,D?ring, Eva,Keul, Marina,Engel, Julian,Tumbrink, Hannah L.,Rauh, Daniel,Laufer, Stefan. "Trisubstituted Pyridinylimidazoles as Potent Inhibitors of the Clinically Resistant L858R/T790M/C797S EGFR Mutant: Targeting of Both Hydrophobic Regions and the Phosphate Binding Site". . p. 5613 - 5637. Retrieved 2017/07/22.