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

Base Information

• Chemical Name: (S)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate
• CAS No.: 128542-75-6
• Molecular Formula: C10H18BrNO2
• Molecular Weight: 264.162
• Hs Code.: 2933990090
• European Community (EC) Number: 859-565-4
• Nikkaji Number: J1.754.084J
• Mol file: 128542-75-6.mol

Synonyms:128542-75-6;(S)-tert-butyl 2-(bromomethyl)pyrrolidine-1-carboxylate;(S)-2-Bromomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester;(S)-N-BOC-2-(BROMOMETHYL)PYRROLIDINE;Tert-butyl (2S)-2-(bromomethyl)pyrrolidine-1-carboxylate;tert-butyl (S)-2-(bromomethyl)pyrrolidine-1-carboxylate;(2S)-1-Boc-2-(bromomethyl)pyrrolidine;SCHEMBL539034;OSMADJAEHVCZKN-QMMMGPOBSA-N;MFCD10566043;AKOS017342954;AM91536;1-Pyrrolidinecarboxylic acid, 2-(bromomethyl)-, 1,1-dimethylethyl ester, (2S)-;AS-37876;CS-0171760;EN300-318446;(S)-tert-butyl-2-(bromomethyl)pyrrolidine-1-carboxylate;(2S)-2alpha-(Bromomethyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

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

Chemical Property:

• PSA: 29.54000
• LogP: 2.71870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 263.05209
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-Tert-Butyl2-(Bromomethyl)Pyrrolidine-1-Carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1CBr
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1CBr

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

There total 10 articles about (S)-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: 95.0%

(S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate (86661-32-7) → (S)-2-(bromomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine (128542-75-6)

Guidance literature:

With lithium bromide; In acetone; for 6h; Reflux;

DOI:10.1002/ejoc.201800886

Reference yield: 70.0%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → (S)-2-(bromomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine (128542-75-6) + 2-chloromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1142400-61-0,403735-05-7)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide; sodium bromide; In dichloromethane; at 25 ℃; for 0.666667h;

DOI:10.1021/ol017168p

Reference yield: 65.0%

N-(tert-butoxycarbonyl)-L-prolinol (69610-40-8) → (S)-2-(bromomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine (128542-75-6)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; Cooling with ice;

DOI:10.1021/acs.jmedchem.7b00316

upstream raw materials:

tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate

N-(tert-butoxycarbonyl)-L-prolinol

di-tert-butyl dicarbonate

(S)-1-Pyrrolidin-2-yl-methanol

Downstream raw materials:

(S)-2-<(acetylthio)methyl>-1-<(tert-butyloxy)carbonyl>pyrrolidine

2-[4-(4-benzoylamino-phenoxy)-6-methoxy-quinolin-7-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-N-tert-butoxycarbonyl-2-[bis(2-methylphenyl)phosphinomethyl]pyrrolidine

adamantan-1-yl-((S)-1-{2-[(dicyclohexylphosphino)methyl]pyrrolidin-1-yl})-methanone

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.
• 2、 Xu, Da-Zhen,Liu, Yingjun,Shi, Sen,Wang, Yongmei. "Chiral quaternary alkylammonium ionic liquid [Pro-dabco][BF4]: As a recyclable and highly efficient organocatalyst for asymmetric Michael addition reactions". experimental part. p. 2530 - 2534. Retrieved 2011/03/17.