Triacetoxyperiodinane → Pyridine-2-carboxylic acid-4-formyl-benzylamide

HRID 970941Notes

Reaction equation

HRID 970941 reaction equation
[OH:1][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[CH:17][CH:18]=1)=[O:1]

Participants

8

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22601292Pyridine-2-carboxylic acid 4-hydroxymethyl-benzylamide

Product 1

HCID 22601372Pyridine-2-carboxylic acid-4-formyl-benzylamideYield 85%

Reagents, catalysts & solvents 5

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of pyridine-2-carboxylic acid-4-hydroxymethyl-benzylamide (360 mg, 1.48 mmol) in anhydrous CH2Cl2 (10 mL) was added Dess-Martin periodiane (690 mg, 1.63 mmol) and the reaction stirred at room temperature for 1 h. The mixture was diluted with diethyl ether (25 mL), ethyl acetate (25 mL), saturated aqueous sodium bicarbonate (15 mL) and saturated aqueous sodium thiosulfate (15 mL) and stirred for 30 minutes. The phases were separated and the aqueous phase washed with ethyl acetate (1×15 mL). The combined organic layers were washed with brine (1×20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the crude oil by column chromatography on silica gel (CH2Cl2) gave the desired aldehyde as a pale yellow oil (300 mg, 85%). 1H NMR (300 MHz, CDCl3) δ 4.76 (d, 2H, J=6.0 Hz), 7.42-7.44 (m, 1H), 7.53 (d, 2H, J=6.0 Hz), 7.87 (d, 2H, J=6.0 Hz), 7.85-7.88 (m, 1H), 8.24 (d, 1H, J=6.0 Hz), 8.55 (br s, 1H), 8.57 (d, 1H, J=3.0 Hz), 10.00 (s, 1H).

Workup

  1. stirringstirred for 30 minutes
  2. customThe phases were separated
  3. washthe aqueous phase washed with ethyl acetate (1×15 mL)
  4. washThe combined organic layers were washed with brine (1×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification of the crude oil by column chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-24018045d54848eca7335d9276053cc9
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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