تفاعل #8841

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   أخرىozone was bubbled into the solution until a blue color
2. 2
   أخرىThe excess ozone was removed with a stream of nitrogen
3. 3
   أخرىthe cooling bath was removed
4. 4
   تركيزThe reaction mixture was then concentrated
5. 5
   أخرىThe residue was then purified by flash chromatography
6. 6
   غسيلeluting with 2:1 heptane/ethyl acetate

الإجراء التجريبي

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).

المصدر