Direct reductive alkylation of amine hydrochlorides with aldehyde bisulfite adducts

被引：5

作者：

Barniol-Xicota, Marta ^{[1
]}

Turcu, Andreea L. ^{[1
]}

Codony, Sandra ^{[1
]}

Escolano, Carmen ^{[2
]}

Vazquez, Santiago ^{[1
]}

机构：

[1] Univ Barcelona, Lab Quim Farmaceut, Unitat Associada CSIC, Fac Farm,Inst Biomed IBUB, E-08028 Barcelona, Spain

[2] Univ Barcelona, Lab Quim Organ, Fac Farm, Inst Biomed IBUB, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 15期

关键词：

Bisulfite adducts; Reductive alkylation; Reductive amination; Sodium cyanoborohydride; AMINATION; CYANOBOROHYDRIDE;

D O I：

10.1016/j.tetlet.2014.03.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild procedure for the direct reaction of aromatic and aliphatic aldehyde bisulfite adducts with primary and secondary amine hydrochlorides in the presence of sodium cyanoborohydride in methanol is reported. (C) 2014 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2548 / 2550

页数：3

相关论文

共 11 条

[1] A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes [J].

Abdel-Magid, Ahmed F. ;

Mehrman, Steven J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) :971-1031

[2] NEW METHOD FOR METHYLATION OF AMINES [J].

BORCH, RF ;

HASSID, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) :1673-&

[3]

Clayden J., 2012, ORGANIC CHEM, P138

[4] Direct Reductive Amination of Aldehyde Bisulfite Adducts Induced by 2-Picoline Borane: Application to the Synthesis of a DPP-IV Inhibitor [J].

Faul, Margaret ;

Larsen, Rob ;

Levinson, Adam ;

Tedrow, Jason ;

Vounatsos, Filisaty .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04) :1655-1659

[5] CYANOBOROHYDRIDE - UTILITY AND APPLICATIONS IN ORGANIC-SYNTHESIS - REVIEW [J].

HUTCHINS, RO ;

NATALE, NR .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1979, 11 (05) :201-+

[6] Counterion effects in the preparation of aldehyde-bisulfite adducts [J].

Kissane, Marie G. ;

Frank, Scott A. ;

Rener, Gregory A. ;

Ley, Christopher P. ;

Alt, Charles A. ;

Stroud, Paul A. ;

Vaid, Radhe K. ;

Boini, Sathish K. ;

McKee, Laura A. ;

Vicenzi, Jeffrey T. ;

Stephenson, Gregory A. .

TETRAHEDRON LETTERS, 2013, 54 (48) :6587-6591

[7] Iron triflate catalyzed reductive amination of aldehydes using sodium borohydride [J].

Kumar, N. Uday ;

Reddy, B. Sudhakar ;

Reddy, V. Prabhakar ;

Bandichhor, Rakeshwar .

TETRAHEDRON LETTERS, 2012, 53 (33) :4354-4356

[8]

LANE CF, 1975, SYNTHESIS-STUTTGART, P135

[9] Expedient Reductive Amination of Aldehyde Bisulfite Adducts [J].

Pandit, Chennagiri R. ;

Mani, Neelakandha S. .

SYNTHESIS-STUTTGART, 2009, (23) :4032-4036

[10]

Smith M.B., 2013, MARCHS ADV ORGANIC C, V7th ed., P1096