A New Route to Bicyclo[1.1.1]pentan-1-amine from 1-Azido-3-iodobicyclo[1.1.1]pentane

被引：32

作者：

Goh, Yi Ling ^{[1
]}

Tam, Eric K. W. ^{[1
]}

Bernardo, Paul H. ^{[1
]}

Cheong, Choon Boon ^{[1
]}

Johannes, Charles W. ^{[1
]}

William, Anthony D. ^{[1
]}

Adsool, Vikrant A. ^{[1
]}

机构：

[1] ASTAR, ICES, Singapore 138667, Singapore

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 07期

关键词：

CATALYZED HYDROHYDRAZINATION; AZIDES; REDUCTION; REVERSAL; HYDRIDE; OLEFINS; POTENT;

D O I：

10.1021/ol500635p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

From a medicinal chemistry perspective, bicyclo[1.1.1]-pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.

引用

页码：1884 / 1887

页数：4

共 40 条

[1] NUCLEOPHILIC-SUBSTITUTION IN 1-SUBSTITUTED 3-IODOBICYCLO[1.1.1]PENTANES - A NEW SYNTHETIC ROUTE TO FUNCTIONALIZED BICYCLO[1.1.1]PENTANE DERIVATIVES [J].

ADCOCK, JL ;

GAKH, AA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6206-6210

[2]

Andrews M.D., 2012, WO Patent, Patent No. [2,012,137,089, 2012137089]

[3]

[Anonymous], 2013, FRAGM 2013 4 RSC BMC

[4] REVERSAL OF STEREOSELECTIVITY IN THE REDUCTION OF GEM-DICHLORIDES BY TRIBUTYLTIN HYDRIDE AND TRIS(TRIMETHYLSILYL)SILANE - SYNTHETIC AND MECHANISTIC IMPLICATIONS [J].

APELOIG, Y ;

NAKASH, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10781-10782

[5] (Me3Si)3SiH-Mediated Intermolecular Radical Perfluoroalkylation Reactions of Olefins in Water [J].

Barata-Vallejo, Sebastian ;

Postigo, Al .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) :6141-6148

[6] U-87947E, A POTENT QUINOLONE ANTIBACTERIAL AGENT INCORPORATING A BICYCLO[1.1.1]PENT-1-YL (BCP) SUBUNIT [J].

BARBACHYN, MR ;

HUTCHINSON, DK ;

TOOPS, DS ;

REID, RJ ;

ZURENKO, GE ;

YAGI, BH ;

SCHAADT, RD ;

ALLISON, JW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (04) :671-676

[7]

Bennett B.L., 2012, [No title captured], Patent No. [WO 2012145569, 2012145569, WO2012145569A1]

[8]

Brewer P. G., 1991, Preparation of 1-Bicyclopentylamine Hydrochloride, U85,879A a Key Intermediate for the Syntheses of Quinolone Antibacterial Agents, Patent No. [TR1510-91-005, 151091005]

[9] Scalable Synthesis of 1-Bicyclo[1.1.1]pentylamine via a Hydrohydrazination Reaction [J].

Bunker, Kevin D. ;

Sach, Neal W. ;

Huang, Qinhua ;

Richardson, Paul F. .

ORGANIC LETTERS, 2011, 13 (17) :4746-4748

[10] AUTOXIDATION OF TRIS(TRIMETHYLSILYL)SILANE [J].

CHATGILIALOGLU, C ;

GUARINI, A ;

GUERRINI, A ;

SECONI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2207-2208

← 1 2 3 4 →