Reacción #8841

Ecuación de reacción

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroozone was bubbled into the solution until a blue color
2. 2
   OtroThe excess ozone was removed with a stream of nitrogen
3. 3
   Otrothe cooling bath was removed
4. 4
   ConcentraciónThe reaction mixture was then concentrated
5. 5
   OtroThe residue was then purified by flash chromatography
6. 6
   Lavadoeluting with 2:1 heptane/ethyl acetate

Procedimiento

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).

Fuente