Efficient cleavage of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2

被引：32

作者：

Strazzolini, P ^{[1
]}

Misuri, N ^{[1
]}

Polese, P ^{[1
]}

机构：

[1] Univ Udine, Dept Chem Sci & Technol, I-33100 Udine, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 12期

关键词：

sulfuric acid; dichloromethane; deprotection; tert-butyl ester; N-Boc-amine;

D O I：

10.1016/j.tetlet.2005.01.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new procedure for the deprotection of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2 is described. The proposed method is simple, cheap, eco-friendly and represents a valid alternative to existing ones, with special significance in large scale applications. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2075 / 2078

页数：4

共 39 条

[21] KOCIENSKI PJ, 1994, PROTECTING GROUPS, P125
[22] Total deprotection of N,N'-bis(tert-butoxycarbonyl)guanidines using SnCl4
Miel, H
Rault, S
[J]. TETRAHEDRON LETTERS, 1997, 38 (45) : 7865 - 7866
[23] A MILD AND EFFICIENT ALUMINA-PROMOTED SYNTHESIS OF TERT-BUTYL ESTERS
NAGASAWA, K
YOSHITAKE, S
AMIYA, T
ITO, K
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (13) : 2033 - 2040
[24] ACTIVATED BASIC ALUMINA PROMOTES A MILD, CLEAN AND HIGH-YIELD RACEMIZATION-FREE SYNTHESIS OF T-BUTYL ESTERS FROM CHIRAL ACID BROMIDES AND T-BUTYL ALCOHOL
NAGASAWA, K
OHHASHI, K
YAMASHITA, A
ITO, K
[J]. CHEMISTRY LETTERS, 1994, (02) : 209 - 212
[25] L-PHENYLALANINE CYCLOHEXYLAMIDE - A SIMPLE AND CONVENIENT AUXILIARY FOR THE SYNTHESIS OF OPTICALLY PURE ALPHA,ALPHA-DISUBSTITUTED (R)-AMINO AND (S)-AMINO ACIDS
OBRECHT, D
BOHDAL, U
BROGER, C
BUR, D
LEHMANN, C
RUFFIEUX, R
SCHONHOLZER, P
SPIEGLER, C
MULLER, K
[J]. HELVETICA CHIMICA ACTA, 1995, 78 (03) : 563 - 580
[26] AMINO-ACIDS AND PEPTIDES .19. SYNTHESIS OF BETA-1-ADAMANTYL AND BETA-2-ADAMANTYL ASPARTATES AND THEIR EVALUATION FOR PEPTIDE-SYNTHESIS
OKADA, Y
IGUCHI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08): : 2129 - 2136
[27] [3+2] cycloaddition of nonstabilized azomethine ylides. 7. Stereoselective synthesis of epibatidine and analogues
Pandey, G
Bagul, TD
Sahoo, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) : 760 - 768
[28] NOVEL GABRIEL REAGENTS
RAGNARSSON, U
GREHN, L
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) : 285 - 289
[29] A SIMPLE ROUTE TO THE SYNTHESIS OF CARBOXYLIC-ACID ESTERS AND THIOL ESTERS BY THE USE OF DIPHOSGENE
RAVI, D
RAO, NR
REDDY, GSR
SUCHETA, K
RAO, VJ
[J]. SYNLETT, 1994, (10) : 856 - 856
[30] Facile and selective O-alkyl transesterification of primary carbamates with titanium(IV) alkoxides
Shapiro, G
Marzi, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7096 - 7097

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