cas 168820-15-3, 1-(3-BROMOBENZYL)PYRROLIDINE | Articles data ｜lookchem

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168820-15-3

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A practical catalytic reductive amination of carboxylic acids
We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.
Andrews, Keith G.,Denton, Ross M.,Hirst, David J.,Stoll, Emma L.,Tongue, Thomas,Valette, Damien
p. 9494 - 9500
(2020/10/02)

Dehydrogenative Aromatization and Sulfonylation of Pyrrolidines: Orthogonal Reactivity in Photoredox Catalysis
Oxidative dehydrogenative aromatization and selective sulfonylation reactions of N-heterocycles under visible-light photoredox catalysis were established. The mild reaction conditions make this approach an appealing and versatile strategy to functionalize/oxidize pyrrolidines whereby arylsulfonyl chlorides were identified to be both catalyst regeneration and sulfonylation reagents.
Muralirajan, Krishnamoorthy,Kancherla, Rajesh,Rueping, Magnus
supporting information
p. 14787 - 14791
(2018/10/20)

METHODS OF PREPARING TOLL-LIKE RECEPTOR MODULATORS
The present invention provides methods of preparing 4-amino-2-biitoxy-8-(3- (pyrrolidin-1-ylmethyl)benzyl)-7,8-dihydropteridin-6(5H)-one and related compounds.
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Paragraph 0216; 0217

(2016/04/09)

Iridium-catalyzed decarboxylative N-alkylation of α-amino acids with primary alcohols
A new decarboxylative N-alkylation reaction of α-amino acids has been developed. A variety of tertiary amines were obtained in good to excellent yields via the decarboxylative N-alkylation reaction of α-amino acids with primary alcohols catalyzed by a CpIr complex. Georg Thieme Verlag Stuttgart New York.
Wu, Jiashou,Jiang, Huajiang,Chen, Dingben,Shen, Jianfen,Zhao, Datong,Xiang, Jing,Zhou, Qizhong
p. 539 - 542
(2014/03/21)

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Chemical Properties

Boiling Point: 284.294 °C at 760 mmHg
Flash Point:125.737 °C
Density: 1.378 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 0.003mmHg at 25°C
Refractive Index: 1.591
PKA: 9?+-.0.20(Predicted)
PSA: 3.24000
LogP: 2.98280

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