tert-Butanol → HCID 86629987, compound

HRID 1013809Notes

Reaction equation

HRID 1013809 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[CH:15]([CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[CH3:35])[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([OH:41])(C)C.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.O=[Os](=O)(=O)=O>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:21]([CH3:35])=[CH:22][C:23]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:24][C:25]=1[CH3:26])[CH2:16][CH:17]=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 23667635Sodium periodateHCID 67318307HCID 67318307, compound

Product 1

HCID 86629987HCID 86629987, compoundYield 418.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of (R)-4-Benzyl-3-[2-(4-benzyloxy-2,6-dimethyl-benzyl)-pent-4-enoyl]-oxazolidin-2-one (7.5 g, 16 mmol) in THF (120 mL) and water (40 mL) with 2.5% OsO4 in tBuOH (16 g, 1.6 mmol). Add Sodium periodate (10 g, 47 mmol) to the solution and stir the reaction for 3 hr at room temperature. Quench the reaction with water and extract with EtOAc. Wash the organic with 1N sodium thiosulfate and brine. Separate the organic, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute the pure product. Remove the solvent to afford 3.25 g (43%) of desired product. MS (m/e): 486 (M+1).

Workup

  1. customthe reaction for 3 hr at room temperature
  2. customQuench
  3. customthe reaction with water
  4. extractionextract with EtOAc
  5. washWash the organic with 1N sodium thiosulfate and brine
  6. customSeparate the organic,
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customremove the solvent
  10. customPurify the crude by silica gel column chromatography
  11. washEtOAc to elute the pure product
  12. customRemove the solvent

Sources & evidence

ORD record
ord-b8fb1de1a0984ec3b22a6f91bb6a0250
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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