Triacetoxyperiodinane → HCID 58636705, compound

HRID 1158971Notes

Reaction equation

HRID 1158971 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:58])[N:29]([CH2:38][C:39]1[CH:40]=[N:41][C:42]([CH3:57])=[C:43]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([C:55]#[N:56])[CH:50]=2)[C:44]=1[CH2:45][OH:46])[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)([CH3:26])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>ClCCl>[C:23]([O:27][C:28](=[O:58])[N:29]([CH2:38][C:39]1[CH:40]=[N:41][C:42]([CH3:57])=[C:43]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([C:55]#[N:56])[CH:50]=2)[C:44]=1[CH:45]=[O:46])[C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58636738HCID 58636738, compound

Product 1

HCID 58636705HCID 58636705, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Dess-Martin periodinone (5.0 g, 11.8 mmol) and [5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (106) (5.26 g, 10.8 mmol) in dichloromethane (200 mL) was stirred at room temperature for 30 minutes. The reaction mixture was then poured into a solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 2:3) as an eluant to give [5-(3-cyano-benzyloxy)-4-formyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (109) (4.6 g, 88% yield) as a colorless solid.

Workup

  1. extractionthe crude product extracted with dichloromethane
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave a crude residue, which
  5. customwas purified by column chromatography on silica gel using
  6. additiona gradient mixture of ethyl acetate:hexane (0:1 to 2:3) as an eluant

Sources & evidence

ORD record
ord-4a612b0bf8ac450e9752b14c86615dab
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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