Ozone → 1-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-one

HRID 1171757Notes

Reaction equation

HRID 1171757 reaction equation
C(OC/C=[C:7]1\[CH2:8][N:9]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:10][CH2:11][CH:12]\1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])(=O)C.[O:28]=[O+][O-]>ClCCl>[C:24]([O:23][C:21]([N:9]1[CH2:10][CH2:11][CH:12]([O:13][Si:14]([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:15])[CH3:16])[C:7](=[O:28])[CH2:8]1)=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 24823OzoneHCID 23138553(E)-3-(2-acetoxyethylidene)-1-(t-butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidine

Product 1

HCID 231387171-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-(2-acetoxyethylidene)-1-(t-butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidine (9.9 g) in dichloromethane (100 ml) was introduced gaseous ozone at −78° C. for 2 hours. After the excess ozone was removed by bubbling nitrogen gas for 1 hour, triphenylphosphine (13 g) was added at the same temperature. The resulting mixture was stirred at room temperature for one hour, and concentrated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (5:1:1 to 1:1:1) as the eluent to afford the title compound as a light yellow oil (4.6 g, yield: 56%).

Workup

  1. customAfter the excess ozone was removed
  2. customby bubbling nitrogen gas for 1 hour
  3. additiontriphenylphosphine (13 g) was added at the same temperature
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel using
  6. additiona mixture of hexane, ethyl acetate and dichloromethane (5:1:1 to 1:1:1) as the eluent

Sources & evidence

ORD record
ord-39c34286abb14e89844ace3147812d11
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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