Deprotection of a primary Boc group under basic conditions

被引：54

作者：

Tom, NJ ^{[1
]}

Simon, WM ^{[1
]}

Frost, HN ^{[1
]}

Ewing, M ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Chem Res & Dev, Groton, CT 06340 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 05期

关键词：

t-butyl carbamate; Boc; sodium t-butoxide; amine; isocyanate;

D O I：

10.1016/j.tetlet.2003.11.108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a primary t-butyl carbamate (Boc) group with excess sodium t-butoxide in slightly wet tetrahydrofuran or 2-methyltetrahydrofuran provides the corresponding primary amine in excellent yield. We believe the reaction proceeds through ail isocyanate intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：905 / 906

页数：2

共 4 条

[1]

Green T.W., 1991, PROTECTIVE GROUPS OR, P309

[2] SYNTHESIS AND REACTIONS OF N-PROTECTED 2-LITHIATED PYRROLES AND INDOLES - THE TERT-BUTOXYCARBONYL SUBSTITUENT AS A PROTECTING GROUP [J].

HASAN, I ;

MARINELLI, ER ;

LIN, LCC ;

FOWLER, FW ;

LEVY, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :157-164

[3] PHOTOCYCLIZATION STRATEGY FOR THE SYNTHESIS OF ANTITUMOR AGENT CC-1065 - SYNTHESIS OF DIDEOXY PDE-I AND PDE-II - SYNTHESIS OF THIOPHENE AND FURAN ANALOGS OF DIDEOXY PDE-I AND PDE-II [J].

RAWAL, VH ;

JONES, RJ ;

CAVA, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :19-28

[4] TRANSAMIDATION REACTIONS USING BETA-LACTAMS - THE SYNTHESIS OF HOMALINE [J].

WASSERMAN, HH ;

BERGER, GD ;

CHO, KR .

TETRAHEDRON LETTERS, 1982, 23 (04) :465-468

← 1 →