Triacetoxyperiodinane → HCID 64997388, compound

HRID 400440Notes

Reaction equation

HRID 400440 reaction equation
[OH:1][CH:2]([CH3:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:1]=[C:2]([CH3:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 43392732HCID 43392732, compound

Product 1

HCID 64997388HCID 64997388, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 154 g N-(2-hydroxy-propyl)-isonicotinamide in 800 mL dichlormethane was added dropwise to a solution of 438 g Dess-Martin reagent in 1.2 L dichlormethane at 0° C. under nitrogen atmosphere. After 30 min at 0° C., the solution was stirred at RT for 4 h. The mixture was concentrated under vacuum and the resulting crude product was purified by flash chromatography (silica gel) to give 91 g of the desired product.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe resulting crude product was purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-f7c3427b54a54b4386403ded79d5bd6a
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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