Title: O-tert-Butyl-N-(chloromethyl)-N-methyl carbamate as a source of the MeNHCH2− synthon
Abstract: The reaction of O-tert-butyl-N-(chloromethyl)-N-methyl carbamate (1) with lithium powder and a catalytic amount of DTBB (2.5 mol %) in the presence of different electrophiles [Me3SiCl, BuiCHO, ButCHO, PhCHO, (CH2)4CO, Et2CO, PhCOMe, Ph2CO] in THF at −78°C leads, after hydrolysis with water, to the expected functionalised carbamates 2. As an example, the hydrolysis of compound 2e with hydrogen chloride affords easy deprotection of the amine functionality yielding the corresponding 1,2-aminoalcohol 3e.
Publication Year: 1996
Publication Date: 1996-07-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 13
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