Ozone → HCID 14988917, compound

HRID 481322Notes

Reaction equation

HRID 481322 reaction equation
[CH:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:18][CH2:17][C:14]3([O:16][CH2:15]3)[CH:13]([C:19]3([CH3:27])[CH:21]([CH2:22][CH:23]=C(C)C)[O:20]3)[CH:12]2[O:28][CH3:29])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:30]=[O+][O-]>CO.ClCCl>[CH:1]1([NH:7][C:8]([O:10][CH:11]2[CH2:18][CH2:17][C:14]3([O:16][CH2:15]3)[CH:13]([C:19]3([CH3:27])[CH:21]([CH2:22][CH2:23][OH:30])[O:20]3)[CH:12]2[O:28][CH3:29])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24823OzoneHCID 14988845HCID 14988845, compound

Product 1

HCID 14988917HCID 14988917, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 6-cyclohexylcarbamoyloxy-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (20 mg) in a mixture of methanol (0.1 ml) and dichloromethane (5 ml) was passed through ozone at -78° C. for 3 minutes. Nitrogen was bubbled into the solution at the same temperature to remove excess ozone. The solvents were evaporated and the residue was dissolved in methanol (2 ml). To the solution was added sodium borohydride (10 mg) in one portion at 5° C. The mixture was stirred at 5° C. for 10 minutes and then concentrated in vacuo. The residue was dissolved in dichloromethane (20 ml), washed with brine, dried, and evaporated. The crude oil was purified by column chromatography on silica gel eluted with diethyl ether to yield 6-cyclohexylcarbamoyloxy-4-[3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2,5]-octane (11.6 mg).

Workup

  1. customNitrogen was bubbled into the solution at the same temperature
  2. customto remove excess ozone
  3. customThe solvents were evaporated
  4. dissolutionthe residue was dissolved in methanol (2 ml)
  5. additionTo the solution was added sodium borohydride (10 mg) in one portion at 5° C
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  8. washwashed with brine
  9. customdried
  10. customevaporated
  11. customThe crude oil was purified by column chromatography on silica gel
  12. washeluted with diethyl ether

Sources & evidence

ORD record
ord-db75b712dad84f3299f182f2190ad43d
Source dataset
uspto-grants-1998_08
Patent number
US05789405

Reaction notes

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