Sodium periodate → HCID 59627525, compound

HRID 1845816Notes

Reaction equation

HRID 1845816 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:13][C:12]([OH:16])(CO)[CH2:11][O:10][C@@H:9]1[C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[F:25])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:13][C:12](=[O:16])[CH2:11][O:10][C@@H:9]1[C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[F:25])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86615516HCID 86615516, compound

Product 1

HCID 59627525HCID 59627525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl[(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (223 mg, 0.59 mmol) in tetrahydrofuran (4 mL) was added a solution of sodium periodate (143 mg, 0.67 mmol) in water (1.3 mL) and the mixture stirred for 3 hours. The mixture was concentrated and purified by flash chromatography (silica, gradient 5-20% ethyl acetate in chloroform) to yield tert-butyl[(2R,3S)-5-oxo-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate as white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (silica, gradient 5-20% ethyl acetate in chloroform)

Sources & evidence

ORD record
ord-7f769083b09a4ac09cbfc690a4bc0862
Source dataset
uspto-grants-2015_02
Patent number
US08951965B2

Reaction notes

Loading…