Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran

被引：35

作者：

Pace, Vittorio ^{[1
,2
]}

Alcantara, Andres R. ^{[2
]}

Holzer, Wolfgang ^{[1
]}

机构：

[1] Univ Vienna, Dept Drug & Nat Prod Synth, Fac Life Sci, A-1090 Vienna, Austria

[2] Univ Complutense, Organ & Pharmaceut Chem Dept, Fac Pharm, E-28040 Madrid, Spain

来源：

GREEN CHEMISTRY | 2011年 / 13卷 / 08期

关键词：

SUPERCRITICAL CARBON-DIOXIDE; REAGENTS; ALDOL; ACID; THF; KF;

D O I：

10.1039/c1gc15574a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A straightforward chemoselective protection of anilines as N-TBS derivatives is described by using a suitable deprotonation of the amine with methyllithium in the environmentally friendly and safer substitute of THF, 2-methyltetrahydrofuran, under exceptional mild reaction conditions (0 degrees C, 30 min). Interestingly, the protecting group maybe cleaved efficiently by simple treatment of N-TBS- anilines with silica gel in ethanol-water.

引用

页码：1986 / 1989

页数：4

共 39 条

[1] The reactivity of the N-Boc protecting group:: an underrated feature
Agami, C
Couty, F
[J]. TETRAHEDRON, 2002, 58 (14) : 2701 - 2724
[2] Preparation and reactions of 2,4,6-tris(trifluoromethyl)phenylamine
Ahlemann, JT
Roesky, HW
Noltemeyer, M
Schmidt, HG
Markovsky, LN
Shermolovich, YG
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1998, 87 (01) : 87 - 90
[3] CONSIDERED AS REAGENTS AND SYNTHETIC METHODS .46. 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE(DBU) - AN EFFECTIVE BASE FOR THE INTRODUCTION OF TERT-BUTYLDIMETHYLSILYL GROUP IN ORGANIC-COMPOUNDS
AIZPURUA, JM
PALOMO, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (04) : 475 - 476
[4] Green Chemistry: Principles and Practice
Anastas, Paul
Eghbali, Nicolas
[J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) : 301 - 312
[5] Toxicological Assessment of 2-Methyltetrahydrofuran and Cyclopentyl Methyl Ether in Support of Their Use in Pharmaceutical Chemical Process Development
Antonucci, Vincent
Coleman, John
Ferry, James B.
Johnson, Neil
Mathe, Michelle
Scott, Jeremy P.
Xu, Jing
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (04) : 939 - 941
[6] Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions
Aycock, David F.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) : 156 - 159
[7] CYCLOREVERSIONS OF ANIONS FROM TETRAHYDROFURANS - CONVENIENT SYNTHESIS OF LITHIUM ENOLATES OF ALDEHYDES
BATES, RB
POTTER, DE
KROPOSKI, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (04) : 560 - &
[8] Industrial solvents and liver toxicity: Risk assessment, risk factors and mechanisms
Brautbar, N
Williams, J
[J]. INTERNATIONAL JOURNAL OF HYGIENE AND ENVIRONMENTAL HEALTH, 2002, 205 (06) : 479 - 491
[9] Asymmetric Deprotonation using s-BuLi or i-PrLi and Chiral Diamines in THF: The Diamine Matters
Carbone, Giorgio
O'Brien, Peter
Hilmersson, Goran
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) : 15445 - 15450
[10] CHIARA JL, 2007, SCI SYNTHESIS, V31, P1697

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