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

HRID 1044337Notes

Reaction equation

HRID 1044337 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-5623d41475a7483ab6a6685bceb6ee8b
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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