Water → HCID 59226578、化合物

HRID 1920228ノート

反応式

HRID 1920228 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 59226578HCID 59226578、化合物

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

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 (0.08 M) 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.

後処理

  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 (0.08 M)
  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%)

出典と根拠

ORDレコード
ord-eaef5fd2975f473f811a9a5ff070c783
出典データセット
uspto-grants-2012_05
特許番号
US08168794B2

反応ノート

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