O-TERT-BUTYL-N-(CHLOROMETHYL)-N-METHYL CARBAMATE AS A SOURCE OF THE MENHCH(2)(-) SYNTHON

Authors
GUIJARRO A ORTIZ J YUS M
Citation
A. Guijarro et al., O-TERT-BUTYL-N-(CHLOROMETHYL)-N-METHYL CARBAMATE AS A SOURCE OF THE MENHCH(2)(-) SYNTHON, Tetrahedron letters, 37(31), 1996, pp. 5597-5600
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
31
Year of publication
1996
Pages
5597 - 5600
Database
ISI
SICI code
0040-4039(1996)37:31<5597:OCAASO>2.0.ZU;2-V
Abstract
The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) w ith lithium powder and a catalytic amount of DTBB (2.5 mol %) in the p resence of different electrophiles [Me(3)SiCl, Bu(i)CHO, Bu(t)CHO, PhC HO, (CH2)(4)CO, Et(2)CO, PhCOMe, Ph(2)CO] in THF at -78 degrees C lead s, after hydrolysis with water, to the expected functionalised carbama tes 2. As an example, the hydrolysis of compound 2e with hydrogen chlo ride affords easy deprotection of the amine functionality yielding the corresponding 1,2-aminoalcohol 3e. Copyright (C) 1996 Elsevier Scienc e Ltd