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21.2.2.1.5 Method 5: Amidation of Esters

DOI: 10.1055/sos-SD-021-00215

Luzzio, F. A.Science of Synthesis, (200521265.

4-Substituted glutarimides (piperidine-2,6-diones) are useful intermediates in the synthesis of natural products such as sesbainimide (11). Using 3-substituted glutaric acid diesters 12 as substrates, direct conversion into the corresponding glutarimides 13 can be effected with sodium amide in liquid ammonia (Scheme 9).[‌14‌] The synthesis of actiketal (14) uses the diester 15 as a key intermediate. The latter compound can be cyclized to the glutar­imide 16 through a multi-step procedure (Scheme 9).[‌15‌]

Meeeee 8 Meeeeeeeeee Meeeeeeee eeee 8-Meeeeeeeeee Meeeeeee Meee Meeeeeee[‌88‌,‌88‌]

Me eeeeeee eeeeeeee ee eeeeeeeeeeee (88) e eeeeeeeeeee eeeeeee eeeeeeee eeeeeeee ee ­eeeeeeeeeeeee eeee eee eeeeeeeeeee eeeeeeeeeee eeeee 88 eeeee eee 8-eeeeeeeeeee eeeeee­eeeee 88 (Meeeee 88). Mee eeeeeee eeeeeeeeee eeee ee eeeeeeeee eeee e eeeeeeee eeee eee eeeeeee e eeeee eeeeee ee eeeeeeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeee Meeeeeeee ee Meeeeee Meeeeeee/Meeeeeeeeee ee Meeeeeeeeee Meeeee eee Meeeeeeeeeeee[‌88‌]

M eeeeeee eeeeeee eeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeeee eeeeeeee eeeeeeeeeee ee M-(eeeeeeeeeee)eee-8-eeeeeee (88) eeeeee 8-eeeeeeeeeeeeeeee (88) (Meeeee 88). Mee eeeeeeeeeee eeeeeee eeee e 8-eee-eeee eeeeeee eeeeeeee eee eeee eeeeeeeee eeee eeeeee.[‌88‌]

Meeeee 88 Meeeeee Meeeeeeeeee ee M-(Meeeeeeeeee)eee-8-eeeeeee[‌88‌]

Meeeeee eeeeeeeee eeeeeee eeeeeeeeee eeeeeeeeeee eeeeee eee eeeee eeeeeeeee eee eeeeeeeeeeee eeeeeeeee ee eee eeeeeeeeee, eee eeee eee eeeeeeeeeeeee eeeeee; eee eeeeeee, eee eeeeeeee ee eee eeeee 88 eeee eeeeee eeeeeeeeee eeeee eee eeeeeeeeeeeeeeeeee eeeeeeeeeee 88 ee 88% eeeee. Meeeeeeee, eee eeeeeeee ee eeeee 8-eeeeeeeeeeeeeeeeeeeee eeee eee eeee eeeee eeeee eee 8-eeeeeeeeeeeeeeeeeeee 88 ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeee ee Meeeeeeeeeee eeee Meeeee Meeeeeee[‌88‌]

M eee-eeeeee eeee eeeeeeeee ee β-eeeeeee 88 eeeeeeeeee e eeeeeeee eeeeeeeeeee ee eeee eeeeeeeeeeee eeeeeeee eeeee eeeeeeeee eeee eeeeeeeee eeee-eeeeeeee ee eee eeeeeeee ee eeee-eeeee eeeeee eeeeeeee, eeeeeeee ee eeeeeeeeeeeee eeee eeeeeeeeeeeeeee eeee. Meee eee eeeeeeee eeeee ee eeeeeeeeeeee, eeeeeeee ee eee eeeeee eeee eeeeee ee eeeeee eeeeeeeeeeeee ee eee eeee 88. Meeee eeeeeee e Meeeeee eeeeeeee ee eeee-eeeee eeeeee eeeeeeee, eee eeee eeeeeeeeee eeeeeeeeeeee eeeee eee eeeeee eeeee eeeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeeeee, eeeee eee eeeeeeeeeee ee eeee eee eeeee 88 (Meeeee 88).[‌88‌] Mee eeeeeeeee eeeeeee ee eeee eeeeee eeeeeeeee eeeeeeee eeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeeeeee ee eee eeeee 88 eee eeeeeeee, eee eeeeeeee ee eeeeeee eeee ee eeeeeeee eeee ee eeee eeeeeeeeeeeeeee eeee ee eeeeee eeee eeeeeeeeeee ee ee 88°M eee 88eeeee eee eeeeeeeeeeee. Meeeeeeeee, eee eeeeee eeeeeeeeeee eeee ee eeeee eeeee ee eeeeee ee eeeeeeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeeee ee M8 eeee ee8 ee ee8 ee e eeeeeeee eeeeeee eeeeee ee M-eeeeeeeeeee ee eee M8 eeeeeeee eeeee.

Meeeee 88 Mee-Meeeee Meee Meeeeeeee ee Meeeeee ee Meeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeee (Meeeeeeeee-8,8-eeeeee) 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeee eeeeeeeeee eeeeeee ee eeeeeeee ee eeeeeee ee eeeeeeee ee eee eee eee eeee ee e eeeeee eeeeeeee.

M eeeeeeee eeeeeee-8,8-eeeeee 88 ee MMM (88eM) eee eeeee ee 88°M ee e eeeeeee eeee ee MeMM8 (8eeee), eeeeeeee ee eeee ee eee eeeeeeee ee Me (88ee) ee eee MM8 (88eM) eeeeeeeeee e eeeeeeeee eeeeee ee MeMe8. Meeee eeeeeeee eee 8e, MM8Me (888ee) eee eeeee eee eee MM8 eee eeeeeee ee eeeeeeeee. M8M (88eM) eee eeeee ee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeee MMMe8 (8 × 88eM). Mee MMMe8 eeeeeeee eeee eeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeeeee eee eeeee eeeeeeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8/eeeeeee 8:8).

8-{(8eM,8M,8M,8eM)-8-(eeee-Meeeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeeeeeee[8,8-e][8,8]eeeeee-8-ee}eeeeeeeeee-8,8-eeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Me8MeM eee eeeee (ee eeeee ee e eeeeeee eeee) eeee e eeeeee ee 88e ee eee eeeee 88 (888ee, 8.88eeee) eee eeeeeeeeeeeee (888ee, 8.8eeee) ee eee MeMM (8.8eM) eeeee M8, eeeee eeeeeeeeeee eee eeeeeee eeee e eeeeeeee eeee. Meeee eeeeeee ee eeeeeeeee ee eeeeeeee eeeeeeeeeeee eeeeeee eeeeee eee MeMM, eee MeMM eeeee eee eeeeeee eeeeeee eeee MM8Me8, eee eeee eeeeee eeee M8M, eeeee, eee eeeeeeeeeeee ee eeeeee eeeeeeeeeee. Meeeeeeee ee eee eeeee eeeeeee eeeee eee eeee eeeeeeeeee, eeeeeeee ee eeeeeee ee 888°M ee eeeeeee eeee, eeeee eee eeee eeeeee eee eeeeeeeeeeeeeee eeeeeeeeee, eee 8-eeeeeeeeeee eeeeeeeeeee 88; eeeee: 88% (eeeeeeee eeee 8% eeeeeeee eeeeeeee).

8-(Meeeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeeee-8,8-eeeee (88); Meeeeee Meeeeeeee:[‌88‌]

Meeeee eeeeeeeeee (8.88eM, 88eeee) eee eeeee ee e eeeeeeeeee ee eee eeeee 88 (88.88e, 88eeee) ee eee MeMM (888eM). Mee eeeeeeeeee eee eeeeeee ee ee eee, eeeee 88e, eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM (8 × 88eM), eee eeee Me8M (8 × 88eM), eee eee-eeeee ee eeeeee eee eeeee eeeeeeee; eeeee: 88.88e (88%).

M-[8,8-Meeee-8-(eeeeeeeeeeeeeeeeeeeeeeeeee)-8-eeeeeeeee]eeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeeeee ee eee eeeee 88 (8.888e, 8.8eeee) eee eeeee-8-eeeeeeeeeeeeeeeeeeeee (8.888e, 8.8eeee) ee eee MeMM (8eM) eee eeeeeee ee ee eee 88e. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM (8 × 8eM), eee Me8M (8 × 8eM), eee eee-eeeee. Mee eeeee eeeeeee eeeeeeee eeee MeMM (8M MMM), eee eeeeeeeeeeeeeee (MMM) eeee eee eeee eeeee eeeeeeee; eeeee: 8.88e (88%).

8-(8-Meeeeeeeeeeee)-8,8-eeeeeeeeeeeeeee-8-eeeeeeeeee Meeee 88; Meeeeee Meeeeeeee:[‌88‌]

Mee 8-(8-eeeeeeeeeeeee)eeeeeeeee-8-eee 88 (8.8 eeeee) eee eeeee eeee eeee-eeeee eeeeee eeeeeeee (8.8 eeeee) ee eee MMM eee eeeeee ee 8°M. 8M e-MeMM (8.8 eeeee) ee MMM eee eeeee eeeeeeee ee eee eeeeeee, eee eeeee 8.8e, eee eeee eee eeeeee ee ee. Meeeeeeee eee eeeeeeee eee eeeeeeee eeeeee 88e. Mee eeeeeeeeeeeeee eeeee ee eee eeeeeee eeeeee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee eeee ee eeeeeeeee eeee eeee MMM ee ee eee 8e, eeeee ee eeeeee.

References