Reaction #8841

Reaction equation

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

Conditions

Workup

1. 1
   Otherozone was bubbled into the solution until a blue color
2. 2
   OtherThe excess ozone was removed with a stream of nitrogen
3. 3
   Otherthe cooling bath was removed
4. 4
   ConcentrationThe reaction mixture was then concentrated
5. 5
   OtherThe residue was then purified by flash chromatography
6. 6
   Washeluting with 2:1 heptane/ethyl acetate

Procedure

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).

Source