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40.5.2.1.2.3 Method 3: Alkylation of N-Alkoxycarbamates

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401038.

tert-Butoxycarbonyl-protected benzyloxyamine 432 reacts with a variety of alkylating agents to produce tert-butyl N-(benzyloxy)carbamates 433 in high yields, which upon subsequent acidic deprotection cleanly deliver N-alkyl-O-benzylhydroxylamines 434 (Scheme 174).[‌614‌‌619‌]

Meeeee 888 Meeeeeeee ee M-Meeee-M-eeeeeeeeeeeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 888

M8 Meeeeee Meeee (%) ee 888 Mee
Me 88 [‌888‌‌888‌]
MM8MM=MM8 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
(MM8)8Me 88 [‌888‌]
(MM8)8MM8Me 88 [‌888‌]
MM(Me)(MM8)8eMe 88 [‌888‌]

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

Meeeee 888 M-Meeee-M-eeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeee M-eeeee-M-eeeeeeeeeeeeeeeeeeeeeeee 888 eee M-eeeee-M-eeeeeeeeeeeeeeeeeeeeeeee 888 eee eeeeeeee ee eeee eeeeee eeee eeeeee eee M-eeeeeeeeee-M-eeeeeeeeeeeeeeee 888 ee eee M-eeeeeeeeee-M-eeeeeeeeeeeeeeee 888 ee eeeeeeeeee eeee eeeee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee, eee eeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeee 888 ee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-Meeee-M-eeeeeeeeeeeeeeeeeeeeeeee eee M-Meeee-M-eeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeee ee eeeeeeeee 888 ee eeeeeeeeeeeeeee eeee, eeeeeeee ee eeeeeeeeeeee eeee, eeeeeeee M-(eeeeeeeee)eeeeeee-8,8-eeeeeee eeeeeeeeeeeeeee (888) ee 88% eeeee,[‌888‌] eeeee ee e eeeeeeee eeeee eee eeeeeeeeeeeeee M[‌888‌,‌888‌,‌888‌] eee eeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-(Meeeeeeee)eeeeeee-8,8-eeeeeee Meeeeeeeeeeeeee[‌888‌]

Me eeeeeeeee eeeeee eee eee eeeeeeeeeee eee eeeeeeeeeeee ee M,M-eeeeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (888) eeeeeeee eeeeeeee ee eeeeee M-eeeeeeeeeeeeeeee eeee eeeeeeee eeeeeee, eeeee eeeeeeeeeeee ee eee eeeeeeeeeeee eeeeee eeeeeee(eeeeee)eeeeeeeee, eeeeeeeeee eeeeeeeeee ee eeeeee eeeeeeeee ee eeeee/eeeeeeee ee 8888°M, eee eeeee eeeeeeeee eeee eeeeeee eeeeeeeeeeee eeee (Meeeee 888). Meeeeeeeeeeee, eeeeeeeeeeee ee eeeeeee ee eeeeeeeee eeee eeeeeee, eeeeeeeeeeee, ee eeeeeeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeee ee M,M-Meeeeeeeeeeeeeeeeeeee Meeeeeeeeeeee eee Meeee M,M-Meeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌]

M eeeeee ee M,M-eee(eeeeeeeeee)eeeeeeeeeeeeee 888, eeee eeeee eeeeeeeeeee eeeeeeee eeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeee ee eeeee eeeeeeeeeeeeeeee (M-eeeeeeeeeeeeeee) eee eeeeeeeeee eeeeeeee eeeeeeeeee.[‌888‌] Meeeeeeeeee, eeeee eeeeeee(eeeeee)eeeeeeeee (M-eeeeee-M-eeeeeeeeeeeeeee) ee eeeee eeeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeeee 888, eeeeeeee eeeeee eee e eeeeeee ee eeeeeeeeeeee eeeeeeeeee eee eeeeeeeeee.[‌888‌]

Meee M-eeeeee-M-(eeeeeeeeeee)eeeeeeeeeeeeee 888 eee eeeeeeee ee eeeeeeee ee eeee eeeeee ee eeeeeeee ee M-eeeeeeeeeee eeeeeeeeeeeeeeeee 888 eeee eeeeeeeeeee, eeeeeeee ee eeeeeeee eeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-Meeeee-M-(eeeeeeeeeee)eeeeeeeeeeeeee[‌888‌]

Me eeeeeeeee eeeeeeeeeee ee M-eeee-eeeee-M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (888), eeeeeeee eee eeeeeeee Meeeeee eeeeee, ee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeeee 888, eeeeeeeee 888 ee 88% eeeeeee eeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee M-eeee-Meeee-M-eeeeeeeeeeeeeeeeeee Meeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

M-Meeeee-M-(8-eeeeeeeeeee)eeeeeeeeeeeee [888, M8=(MM8)8Me]; Meeeeee Meeeeeeee:[‌888‌]

MeM (888ee, 88eeee) eee eeeee ee e eeeeeee eeee ee 888 (8.88e, 88eeee) ee eeeee MMM (88eM) eee eee eeeeeee eee eeeeeee ee ee eee 88eee. 8-Meeee-8-eeeeeeeeeeee (8.88e, 88eeee) eee eeeee eee eeeeeeee eee eeeeeeeee ee ee eee e eeeeeee 88e. Meeeeeeeee eee eeeeeee eee eeeeee eeee M8M eee eee eeeeeee eee eeeeeeeee eeee eeeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee 888 [M8=(MM8)8Me] ee e eeee eeeeee eee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/Me8M 88:8); eeeee: 8.8e (88%).

Meeeeeeee 888 (8.8e, 88eeee) eee eeeee ee e eeeeeee ee MM8Me8/MMM (8:8) eee eee eeeeeee eee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeee eeee eeeeeeee eeee 8M MeMMM8 eeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeee eeee eeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeeeee e eeee eeeeee eee; eeeee: 8.88e (88%); MM (eeee) ν̃eee: 8888, 8888, 8888, 8888, 8888ee8; 8M MMM (MMMM-e8, δ): 8.88 (e), 8.88 (e), 8.88 (e), 8.88 (e), 8.888.88 (e).

References


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