Reductive Amination in the Synthesis of Pharmaceuticals

被引：577

作者：

Afanasyev, Oleg, I ^{[1
]}

Kuchuk, Ekaterina ^{[1
]}

Usanov, Dmitry L. ^{[2
]}

Chusov, Denis ^{[1
,3
,4
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova St 28, Moscow 119991, Russia

[2] Broad Inst MIT & Harvard, 415 Main St, Cambridge, MA 02142 USA

[3] Natl Res Univ Higher Sch Econ, Miasnitskaya Str 20, Moscow 101000, Russia

[4] Peoples Friendship Univ Russia, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

CHEMICAL REVIEWS | 2019年 / 119卷 / 23期

关键词：

PEPTIDASE-IV INHIBITOR; LARGE-SCALE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; PRACTICAL SYNTHESIS; CATALYTIC SYNTHESIS; SODIUM-BOROHYDRIDE; KINETIC RESOLUTION; AMINO-ACID;

D O I：

10.1021/acs.chemrev.9b00383

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reductive amination plays a paramount role in pharmaceutical and medicinal chemistry owing to its synthetic merits and the ubiquitous presence of amines among biologically active compounds. It is one of the key approaches to C-N bond construction due to its operational easiness and a wide toolbox of protocols. Recent studies show that at least a quarter of C-N bond-forming reactions in the pharmaceutical industry are performed via reductive amination. This Review concisely compiles information on 71 medical substances that are synthesized by reductive amination. Compounds are grouped according to the principle of action, which includes drugs affecting the central nervous system, drugs affecting the cardiovascular system, anticancer drugs, antibiotics, antiviral and antifungal medicines, drugs affecting the urinary system, drugs affecting the respiratory system, antidiabetic medications, drugs affecting the gastrointestinal tract, and drugs regulating metabolic processes. A general synthetic scheme is provided for each compound, and the description is focused on reductive amination steps. The green chemistry metric of reaction mass efficiency was calculated for all reactions.

引用

页码：11857 / 11911

页数：55

共 325 条

[31] Coumarins from Free ortho-Hydroxy Cinnamates by Heck-Matsuda Arylations: A Scalable Total Synthesis of (R)-Tolterodine [J].

Barancelli, Daniela A. ;

Salles, Airton G., Jr. ;

Taylor, Jason G. ;

Correia, Carlos Roque D. .

ORGANIC LETTERS, 2012, 14 (23) :6036-6039

[32] Syntheses of Cinacalcet: An Enantiopure Active Pharmaceutical Ingredient (API) [J].

Barniol-Xicota, Marta ;

Leiva, Rosana ;

Escolano, Carmen ;

Vazquez, Santiago .

SYNTHESIS-STUTTGART, 2016, 48 (06) :783-803

[33] Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2004, 6 (22) :3973-3975

[34] The First Large-Scale Synthesis of MK-4305: A Dual Orexin Receptor Antagonist for the Treatment of Sleep Disorder [J].

Baxter, Carl A. ;

Cleator, Ed ;

Brands, Karel M. J. ;

Edwards, John S. ;

Reamer, Robert A. ;

Sheen, Faye J. ;

Stewart, Gavin W. ;

Strotman, Neil A. ;

Wallace, Debra J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (02) :367-375

[35]

Bays D. E, 1983, U.S. Patent, Patent No. [4,399,294 A, 4399294]

[36] Recoverable resin-supported pyridylamide ligand for microwave-accelerated molybdenum-catalyzed asymmetric allylic alkylations: Synthesis of baclofen [J].

Belda, O ;

Lundgren, S ;

Moberg, C .

ORGANIC LETTERS, 2003, 5 (13) :2275-2278

[37]

Berger M. S, 2005, WO Patent, Patent No. [WO2005120512 (A2), 2005120512]

[38]

Berger M. S, 2005, WO Patent, Patent No. [WO2005120504 (A2), 2005120504]

[39] REDUCTIVE ALKYLATIONS OF DIMETHYLAMINE USING TITANIUM(IV) ISOPROPOXIDE AND SODIUM-BOROHYDRIDE - AN EFFICIENT, SAFE, AND CONVENIENT METHOD FOR THE SYNTHESIS OF N,N-DIMETHYLATED TERTIARY-AMINES [J].

BHATTACHARYYA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4928-4929

[40] β-Substituted γ-butyrolactams from mucochloric acid: synthesis of (±)-baclofen and other γ-aminobutyric acids and useful building blocks [J].

Biswas, Kallolmay ;

Gholap, Rajesh ;

Srinivas, Padakanti ;

Kanyal, Sachin ;

Das Sarma, Koushik .

RSC ADVANCES, 2014, 4 (05) :2538-2545

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