Ozone → tert-Butyl 4-(1-hydroxyl-2-oxoethyl)-2-methyl-3-oxopiperidine-1-carboxylate

HRID 132871Notes

Reaction equation

HRID 132871 reaction equation
[O:1]=[O+][O-].[OH:4][CH:5]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]([CH3:27])[C:15]1=[O:28])/[CH:6]=C/C1C=CC=CC=1>CO.ClCCl>[OH:4][CH:5]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH:16]([CH3:27])[C:15]1=[O:28])[CH:6]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 69220534tert-Butyl 4-[(2E)-1-hydroxyl-3-phenylprop-2-enyl]-2-methyl-3-oxopiperidine-1-carboxylate

Product 1

HCID 86604215tert-Butyl 4-(1-hydroxyl-2-oxoethyl)-2-methyl-3-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone gas was bubbled into a solution of 0.450 g (1.30 mmol) of tert-butyl 4-[(2E)-1-hydroxyl-3-phenylprop-2-enyl]-2-methyl-3-oxopiperidine-1-carboxylate (Step D) in 10 mL of methanol and 10 mL of dichloromethane at −78° C. until the solution turned blue. The reaction was quenched with dimethyl sulfide, warmed to ambient temperature, and stirred for 1 h. The mixture was concentrated in vacuo and purified by flash chromatography on a Biotage® system (silica gel, eluting with 20% ethyl acetate/hexane to 60% ethyl acetate/hexane), affording the title compound.

Workup

  1. customThe reaction was quenched with dimethyl sulfide
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on a Biotage® system (silica gel, eluting with 20% ethyl acetate/hexane to 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-484f189c99434bcf9f8fa9831af6343b
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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