Sodium periodate → HCID 131724982, compound

HRID 1070587Notes

Reaction equation

HRID 1070587 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[C:17]([CH2:18][CH2:19][CH:20]=C)=[C:16]2[C:11]([CH2:12][CH2:13][C@H:14]([C:22]([CH3:30])([CH3:29])[O:23][SiH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[O:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:33].[Na+]>O1CCCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:7]1[C:8]2[C:17](=[C:16]3[C:11](=[CH:10][CH:9]=2)[CH2:12][CH2:13][C@H:14]([C:22]([CH3:30])([CH3:29])[O:23][SiH2:24][C:25]([CH3:28])([CH3:26])[CH3:27])[O:15]3)[CH2:18][CH2:19][CH:20]1[OH:33])=[O:31])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 131724980HCID 131724980, compound

Product 1

HCID 131724982HCID 131724982, compoundYield 81.2%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-[8-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-chroman-7-yl]-carbamic acid tert-butyl ester (3.6 g, 8.0 mmole) in tetrahydrofuran (150 mL) and water (15 mL) at 0° C. was added osmium tetroxide (0.4 mL, 5% in water), followed by sodium periodate (5.16 g, 24 mmole). The mixture was stirred for 6 hours. The solution was diluted with ethyl acetate and the organic layer was washed with water, dried over sodium sulfate, filtered, and the solvent evaporated in vacuum. Column chromatography on silica gel (10% ethyl acetate/hexane) afforded 2.92 g (81%) of the title compound as an oil, [α]25D=−36.75° (4.9, THF).

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-144c093b9e214978ba959ad5a8b9d6ec
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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