Реакция #8841

Уравнение реакции

methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

methanol

methyl sulfide

→

title compound

Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Условия реакции

Обработка

1. 1
   Другоеozone was bubbled into the solution until a blue color
2. 2
   ДругоеThe excess ozone was removed with a stream of nitrogen
3. 3
   Другоеthe cooling bath was removed
4. 4
   КонцентрированиеThe reaction mixture was then concentrated
5. 5
   ДругоеThe residue was then purified by flash chromatography
6. 6
   Промывкаeluting with 2:1 heptane/ethyl acetate

Методика

A solution of methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (29.4 g, 0.0945 mol) from Step B in methanol (1000 mL) was cooled to −78° C. in a dry ice/methanol bath and ozone was bubbled into the solution until a blue color persisted. The excess ozone was removed with a stream of nitrogen and then methyl sulfide (69 mL, 0.95 mol) was added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was then concentrated. The residue was then purified by flash chromatography eluting with 2:1 heptane/ethyl acetate to afford the title compound (23.0 g).

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