Sodium Thiosulfate → HCID 86614019, compound

HRID 253135Notes

Reaction equation

HRID 253135 reaction equation
[CH2:1]([C@@H:4]1[C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6]([CH3:16])([CH3:15])[N:5]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH:2]=C.I([O-])(=O)(=O)=[O:28].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH3:16][C:6]1([CH3:15])[N:5]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[C@H:4]([CH2:1][CH:2]=[O:28])[C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7]1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 86614020HCID 86614020, compound

Product 1

HCID 86614019HCID 86614019, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the crude (4R,5R)-benzyl 4-allyl-2,2-dimethyl-5-phenyloxazolidine-3-carboxylate (1.29 g, 3.66 mmol) in THF (50 mL) and water (20 mL) was added osmium tetroxide (0.45 ml, 0.0180 mmol, 4%) solution. The reaction was stirred for 10 min, after which sodium periodate (3.91 g, 18.3 mmol) was added portion wise over 1 hr. Stirring was continued for 2 h. Saturated aqueous Na2S2O3 was added and the reaction was stirred for 15 min. The volatiles were removed in vacuo and the aqueous residue extracted with Et2O (3×50 mL). The combined ether layers were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The crude residue was evaporated onto silica gel and purified via flash chromatography (0% to 20%; EtOAc in hexanes) to afford (4R,5R)-benzyl 2,2-dimethyl-4-(2-oxoethyl)-5-phenyloxazolidine-3-carboxylate. MS m/z=354 [M+1]+. Calc'd for C21H23NO4: 353.

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. stirringthe reaction was stirred for 15 min
  4. customThe volatiles were removed in vacuo
  5. extractionthe aqueous residue extracted with Et2O (3×50 mL)
  6. washThe combined ether layers were washed with water (20 mL), brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was evaporated onto silica gel
  11. custompurified via flash chromatography (0% to 20%; EtOAc in hexanes)

Sources & evidence

ORD record
ord-24f6b9e0472a40469743df1789fe77e5
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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