Tetrahydrofuran → (4S)-4-benzyl-3-{[(1R,2R)-2-(4-chlorophenyl)-4-oxocyclopentyl]carbonyl}-1,3-oxazolidin-2-one

HRID 1743943Notes

Reaction equation

HRID 1743943 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:16]1[CH2:20][C:19](=C)[CH2:18][C@H:17]1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:33]CC1.I([O-])(=O)(=O)=O.[Na+].O1CCCC1>CC(C)=O.O.[Os](=O)(=O)(=O)=O.C(OCC)(=O)C>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:16]1[CH2:20][C:19](=[O:33])[CH2:18][C@H:17]1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 68518511(4S)-4-benzyl-3-{[(1R,2R)-2-(4-chlorophenyl)-4-methylenecyclopentyl]carbonyl}-1,3-oxazolidin-2-one

Product 1

HCID 68517729(4S)-4-benzyl-3-{[(1R,2R)-2-(4-chlorophenyl)-4-oxocyclopentyl]carbonyl}-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 25 mL round bottom flask equipped with a magnetic stir bar was charged with 1.980 g (5.00 mmol) of the product of Step B dissolved in 9.0 mL acetone. To the reaction mixture was added 0.702 g (5.99 mmol) of 4-methylmorpholine N-oxide dissolved in 2 mL water followed by 1.6 mL (0.26 mmol) of an osmium tetroxide solution (4 wt % in water). The reaction mixture was stirred 1.5 h at room temperature at which point TLC analysis (25% ethyl acetate-hexanes) indicated complete consumption of the starting material. The reaction mixture was quenched with excess 10% aqueous sodium bisulfite, then partitioned between water and ethyl acetate in a separatory funnel. The organic layer was washed with water, separated, then dried (MgSO4), filtered and evaporated in vacuo. The residual oil was redissolved in 12 mL of 1:1 tetrahydrofuran-water in a 25 mL round bottom flask. To this solution was added 1.282 g (5.99 mmol) of sodium periodate and an aditional 3 mL of tetrahydrofuran. After stirring for approximately 30 min at room temperature, a precipitate formed. Stirring was continued for 1.5 h, at which point TLC analysis (50% ethyl acetate-hexanes) revealed a new less polar product spot. The mixture was suspended between ethyl acetate and water and extracted. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo. The residual clear oil was used in the next step without further purification.

Workup

  1. customA 25 mL round bottom flask equipped with a magnetic stir bar
  2. customconsumption of the starting material
  3. customThe reaction mixture was quenched with excess 10% aqueous sodium bisulfite
  4. custompartitioned between water and ethyl acetate in a separatory funnel
  5. washThe organic layer was washed with water
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe residual oil was redissolved in 12 mL of 1:1 tetrahydrofuran-water in a 25 mL round bottom flask
  11. customa precipitate formed
  12. stirringStirring
  13. extractionextracted
  14. customThe organic layer was separated
  15. dry with materialdried (MgSO4)
  16. filtrationfiltered
  17. customevaporated in vacuo
  18. customThe residual clear oil was used in the next step without further purification

Sources & evidence

ORD record
ord-42f64d5266e84725a134da5ddabc1f50
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Reaction notes

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