Expedient Reductive Amination of Aldehyde Bisulfite Adducts

被引：16

作者：

Pandit, Chennagiri R. ^{[1
]}

Mani, Neelakandha S. ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Dept Drug Discovery, San Diego, CA 92121 USA

来源：

SYNTHESIS-STUTTGART | 2009年 / 23期

关键词：

Bisulfite adducts; reductive amination; sodium triacetoxyborohydride; NEUROPEPTIDE YY2 RECEPTOR;

D O I：

10.1055/s-0029-1217050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, one-pot protocol for the direct reductive amination of aldehyde bisulfite adducts is reported. Bisulfite adducts of aliphatic and aromatic aldehydes, oil treatment with an organic base under non-aqueous conditions liberate the aldehyde in situ, which then undergoes efficient reductive amination with amines in the presence of sodium triacetoxyborohydride.

引用

页码：4032 / 4036

页数：5

共 11 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2]

Baxter E.W., 2002, ORGANIC REACTIONS, V59, P1, DOI [DOI 10.1002/0471264180.0R059.01, DOI 10.1002/0471264180.OR059.01]

[3] A practical, efficient synthesis of 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbaldehyde [J].

Bio, Matthew M. ;

Hansen, Karl B. ;

Gipson, John .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (05) :892-895

[4] Characterization of N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyano-phenyl)-N-[1-(2-cyclopentyl-ethyl)-piperidin-4yl]-acrylamide (JNJ-5207787), a small molecule antagonist of the neuropeptide YY2 receptor [J].

Bonaventure, P ;

Nepomuceno, D ;

Mazur, C ;

Lord, B ;

Rudolph, DA ;

Jablonowski, JA ;

Carruthers, NI ;

Lovenberg, TW .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2004, 308 (03) :1130-1137

[5] STUDIES DIRECTED TOWARD SYNTHESIS OF PLASMALOGENS .2. (+-)-CIS-AND-TRANS-3-(N-HEXADEC-1-ENYLOXY)-1,2-PROPANEDIOL [J].

CRAIG, JC ;

HAMON, DPG .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4168-&

[6] EXPERIMENTS IN THE VERATROLE AND QUINOXALINE GROUPS [J].

EHRLICH, J ;

BOGERT, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1947, 12 (04) :522-534

[7] Novel non-peptidic neuropeptide YY2 receptor antagonists [J].

Jablonowski, JA ;

Chai, WY ;

Li, XB ;

Rudolph, DA ;

Murray, WV ;

Youngman, MA ;

Dax, SL ;

Nepomuceno, D ;

Bonaventure, P ;

Lovenberg, TW ;

Carruthers, NI .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1239-1242

[8] A practical procedure for the synthesis of multifunctional aldehydes through the Fukuyama reduction and elucidation of the reaction site and mechanism [J].

Kimura, M ;

Seki, M .

TETRAHEDRON LETTERS, 2004, 45 (16) :3219-3223

[9] A novel, nonaqueous method for regeneration of aldehydes from bisulfite adducts [J].

Kjell, DP ;

Slattery, BJ ;

Semo, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5722-5724

[10] ASYMMETRIC SYNTHESIS .1. SYNTHESIS AND ABSOLUTE CONFIGURATION OF ALPHA-AMINOALKANESULFONATES DERIVED FROM (-)-EPHEDRINE AND AROMATIC ALDEHYDE BISULFITES [J].

NEELAKANTAN, L .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (16) :2253-+

← 1 2 →