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40.5.2.1.1.6 Method 6: Synthesis from Ethyl N-Hydroxyimidates

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401030.

Hydroximic esters or N-hydroxyimidates, first mentioned by Lossen in 1876,[‌564‌] are selectively alkylated at the NOH group[‌565‌] and therefore offer a facile access to a great variety of O-alkylhydroxylamines by mild acidic hydrolysis of the intermediate O-alkylhydroximic ester.[‌463‌,‌565‌‌573‌] This methodology, with ethyl N-hydroxyacetimidate (395) as the preferred reagent, is successfully applied to the preparation of polyfunctional alkoxyamines of general type 398 with antihypertensive activity.[‌572‌] For example, reaction of 395 with 2-(chloromethyl)oxirane affords 396, which is then treated with O-, S-, or N-nucleophiles to form compounds of type 397. Subsequent acidolysis provides polyfunctional hydroxylamine dihydrochlorides 398 in good yields (Scheme 152).[‌572‌] Analogously, further polyfunctional O-alkylhydroxylamines are obtained as salts or free bases (oils).

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Meeeeeeeeee 888

M-Meeeeeeeeeeeeeeeee 888 Meeeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

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M-(Meee-8-eeee)eeeeeeeeeeeeee 888 eee M-(eeeeeeeee)eeeeeeeeeeeeee eee eeeeeeee eeeeeee eeeeeeeee eee eeeeeeeeeeee 888 ee eeeeeeeeee eeeee M-eeeeeeeeeeeeeeeeee eeee eee eeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeee ee e eeeeeee ee eeeeeee eee eeeeeee eeeeee eeeeeeeee, eeee eeeeeeeeeeeeeeeeee eeeeeee ee e eeeee-eeeeeeee eeeeeeee (Meeeee 888).[‌888‌] Meeeeee, ee eeee eeeee ee eeeeee eee eeeeeeee.

Meeeee 888 Meeeeeeee ee M-(Meee-8-eeee)eeeeeeeeeeeeee eeee Meeee M-Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeee eeee eeeee M-(8-eeeeeeeeeee)eeeeeeeeeee (888),[‌888‌] e eeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eee ee eeeeeeee eee eeeeeeeeeeeee ee eeeeee eeeeeeeeee ee eeeeeeeee eeeeeeeeee. Mee eeeeeee, eeeeeeee ee 888 eeee M,M-eee(8-eeeeeeeeeeeeeeeeeee)eeeeee-8,8-eeeeeee eeeeeee 888, eeeee eeee eeeeeeeeee eeeeeeeee eee(eeeeeeee)eeeeeeee eeeeeeeeeeeeeeeeee (888) ee 88% eeeeeee eeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee Mee(eeeeeeee)eeeeeeee Meeeeeeeeeeeeeeeee eeee ee Meeee M-Meeeeeeeeeeeeeeee[‌888‌]

Meeeeee eeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeee eeeee M-{8-[(8-eeeeeeeeeee)eeeee]eeeeeeeeeeeeeeeee (888), eeeee eeee eeeeeeeee eeee eeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee, eeeeeeee ee eeeeeeeeee, eeeeeeee eee M-eeeeeeeeeeeeeeeeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-[8-(Meeeeeee)eeeee]eeeeee-8,8-eeeeeee Meeeeeeeeeeeeeee eeee ee Meeee M-Meeeeeeeeeeeeeeee[‌888‌]

8-{[8-(Meeeeeee)eeeee]eeeeeeeeee}-8-eeeeeeeeeeeee (888), e eeeeee eeeeeeeeeeee eeeee-eeeeeee eeeeeee, eeeee eeee eee eee eeeeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeeeeeeee eeeeeeee ee eeeeeee eeeee ee eeee eeeeee eeeeeee eeeeeeeeee, ee eeeeeeeeee eeee eeeee M-eeeeeeeeeeeeeeeeee (888) ee eeee eeeee (Meeeee 888).[‌888‌] 8-(Meeeeeee)eee-8-eee-8-eeeee ee eeeeeeee eeeeeeeee ee 88% eeeee.

Meeeee 888 Meeeeeeee ee 8-{[8-(Meeeeeee)eeeee]eeeeeeeeee}-8-eeeeeeeeeeeee eeee Meeee M-Meeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

M-[(8M)-8-Meeeeeeeee-8-eeee]eeeeeeeeeeeee Meeeeeeeeeeee (888, M=M=M; M=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeee M-eeeeeeeeeeeeeeeeee (888; 888e, 8.88eee) ee eeeeeee (888eM) eee eeeee eeeeeeee ee e eeee ee 88% MeMM (888eM) ee M8M (888eM) eeee 88eee. Meee, MMMM (8.8e, 88eeee) eee 88% (M)-8,8-eeeeeeeeeeeeeee (888.8e, 8.88eee) eeee eeeee eeeeeeee eeee 88eee ee 8888°M. Mee eeeeeee eee eeeeeee ee 8888°M eee 8e eee eeeeee ee ee, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee M8M (8 ×) eee eeeee eeeeeeee eeee 888eee ee 8888°M ee e eeee ee 88% MMe (888.8e) ee M8M (88eM). Mee eeeeeee eee eeeeee ee 8888°M eee 888eee, eeee eeeeee ee ee, eee eeeeeeee ee eeee e eeeeeeeee eeeee; eeeee: 88.8e (88%); ee 888888°M.

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