Sodium periodate → (S)-4-(4-Hydroxy-2-methyl-butyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

HRID 130525Notes

Reaction equation

HRID 130525 reaction equation
[CH3:1][CH:2]([CH2:18][CH:19]=C)[CH2:3][C@@H:4]1[CH2:8][N:7]([C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:6](=[O:17])[CH2:5]1.I([O-])(=O)(=O)=[O:22].[Na+]>CC(O)(C)C.C1COCC1.O.O=[Os](=O)(=O)=O>[OH:22][CH2:19][CH2:18][CH:2]([CH3:1])[CH2:3][C@@H:4]1[CH2:8][N:7]([C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:6](=[O:17])[CH2:5]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 54216471(S)-4-(2-Methyl-pent-4-enyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

Product 1

HCID 54144051(S)-4-(4-Hydroxy-2-methyl-butyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

OsO4 (2 mL of a 4% wt solution in t-BuOH) was added to the alkene 88 (5.8 g, 0.021 mol) in THF/H2O (3:1, 100 mL). After 1 hour, sodium periodate (11.4 g, 0.053 mol) was added. After 2 hours, the suspension was filtered and the solids washed with dichloromethane. The filtrate was concentrated and the residue azeotroped with toluene. The residue was dissolved in ethanol and sodium borohydride (2.5 g) added. The suspension was stirred at room temperature 15 overnight. 1N citric acid was added and the mixture diluted with ether. The resultant two layers were separated and the aqueous phase was extracted with ether and the combined organic dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/EtOAc) of the residue gave an oil. 4.2 g, 73%. MS, m/z (relative intensity): 276 [M+H, 100%].

Workup

  1. waitAfter 2 hours
  2. filtrationthe suspension was filtered
  3. washthe solids washed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customthe residue azeotroped with toluene
  6. dissolutionThe residue was dissolved in ethanol
  7. additionsodium borohydride (2.5 g) added
  8. addition1N citric acid was added
  9. additionthe mixture diluted with ether
  10. customThe resultant two layers were separated
  11. extractionthe aqueous phase was extracted with ether
  12. dry with materialthe combined organic dried (MgSO4)
  13. concentrationconcentrated
  14. customFlash chromatography (1:1 hexane/EtOAc) of the residue gave an oil

Sources & evidence

ORD record
ord-b5b70ff91d2748e5bb28e06fbbf2ff86
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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