Ozone → 1-Tert-butyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

HRID 1639955Notes

Reaction equation

HRID 1639955 reaction equation
CC(C)=[CH:3][CH2:4][C:5]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.[O:24]=[O+][O-]>C(Cl)Cl>[O:24]=[CH:3][CH2:4][C:5]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1

Participants

4

Reactant 2

HCID 24823OzoneHCID 579707591-Tert-butyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate

Product 1

HCID 579708781-Tert-butyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate (2.75 g, 8.5 mmol) in CH2Cl2 (100 mL) was cooed to −78° C., and ozone was passed into the reaction mixture until a light blue color was observed (ca. 15 min). Nitrogen was then bubbled through the solution to remove the excess ozone. Dimethyl sulfide (10 mL) was added and the reaction was slowly warmed to room temperature and stirred overnight. The reaction was then washed with water and brine, dried and concentrated to give the product (2.5 g).

Workup

  1. customwas cooed to −78° C.
  2. custom(ca. 15 min)
  3. customNitrogen was then bubbled through the solution
  4. customto remove the excess ozone
  5. additionDimethyl sulfide (10 mL) was added
  6. washThe reaction was then washed with water and brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-62b84bdcec41429eab12011c9cc79157
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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