Water → HCID 59226578, 화합물

HRID 2046827노트

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HRID 2046827 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 59226578HCID 59226578, 화합물

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 22242641Methanol--water (1/1)용매

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온도
0 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-392ec194ab4248db8d1a8c975be356f3
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592455B2

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