Water → HCID 59226578, compound

HRID 73590Notes

Reaction equation

HRID 73590 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH:14]([CH:15]([CH:17]=C)[CH3:16])[O:13][C:12](=[O:19])[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.I([O-])(=O)(=O)=[O:22].[Na+].[BH4-].[Na+]>[Os](=O)(=O)(=O)=O.CO.O>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH:14]([CH:15]([CH3:16])[CH2:17][OH:22])[O:13][C:12](=[O:19])[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 59226487(4R)-4-(benzyloxymethyl)-5-(but-3-en-2-yl)oxazolidin-2-one

Product 1

HCID 59226578HCID 59226578, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4R)-4-(benzyloxymethyl)-5-(but-3-en-2-yl)oxazolidin-2-one (1.0 equiv.) in 2:1 MeOH/H2O (0.04 M) was added osmium tetroxide 4% in H2O (0.07 equiv) and sodium periodate (3.0 equiv.). After stirring for 3 hours, the white precipitate was filtered and rinsed with EtOAc. The combined filtrate was concentrated in vacuo and the residue was dissolved in EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered and concentrated. The crude aldehyde was dissolved in EtOH (0.08M) and upon cooling to 0° C., sodium borohydride (2.0 equiv.) was added. After stirring for 15 hours and coming to room temperature the reaction was quenched by addition of H2O. After stirring for 20 minutes, the EtOH was removed in vacuo, EtOAc was added and the solution was washed with 1N HCl, NaHCO3(sat.) and NaCl(sat.), dried over MgSO4, filtered and concentrated yielding after purification by silica gel chromatography (4R)-4-(benzyloxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one as a 3:1 mixture of isomers (60%). LCMS (m/z): 266.1 (MH+); LC Rt=2.28 min.

Workup

  1. filtrationthe white precipitate was filtered
  2. washrinsed with EtOAc
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with NaCl(sat.)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe crude aldehyde was dissolved in EtOH (0.08M)
  10. stirringAfter stirring for 15 hours
  11. customcoming to room temperature
  12. customwas quenched by addition of H2O
  13. stirringAfter stirring for 20 minutes
  14. customthe EtOH was removed in vacuo, EtOAc
  15. additionwas added
  16. washthe solution was washed with 1N HCl, NaHCO3(sat.) and NaCl(sat.)
  17. dry with materialdried over MgSO4
  18. filtrationfiltered
  19. concentrationconcentrated
  20. customyielding
  21. customafter purification by silica gel chromatography (4R)-4-(benzyloxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one
  22. additionas a 3:1 mixture of isomers (60%)

Sources & evidence

ORD record
ord-a7d55aee624d41fe8bf0d6a98ed17604
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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