Triacetoxyperiodinane → Methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

HRID 15418Notes

Reaction equation

HRID 15418 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[N:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1[N:7]([CH:8]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[N:5][CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 17975627Methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Product 1

HCID 17975636Methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title B compound, methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate (0.60 g, 2.11 mmol) in DCM (7.0 mL) is added Dess-Martin periodinane (15% wt solution, 7.0 mL, 3.2 mmol) and the reaction is stirred for 3 h. The reaction mixture is partitioned between EtOAc and sodium bicarbonate-sodium thiosulfate. The combined organic phases are washed with brine and dried (anhydrous sodium sulfate) and concentrated. The residue is subjected to flash chromatography (silica) eluting with EtOAc:MeOH (9:1) to give methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate as an oil: 1H-NMR (CDCl3) δ 9.68 (1H, s), 8.00 (1H, s), 7.87 (1H, s), 7.65 (2H, d, J=8.5), 7.37 (2H, d, J=8.5), 6.63 (1H, m), 3.66 (3H, s), 3.43 (1H, dd, J=16.5, 8.5), 3.30 (1H, dd, J=16.5, 6.6); 13C-NMR (CDCl3) δ 178.9, 169.2, 144.9, 143.0, 141.8, 132.7, 130.8, 127.4, 118.0, 112.5, 56.5, 52.4, 39.0; e/z (ES) 284 (M+1, 100%).

Workup

  1. customThe reaction mixture is partitioned between EtOAc and sodium bicarbonate-sodium thiosulfate
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. washeluting with EtOAc:MeOH (9:1)

Sources & evidence

ORD record
ord-8d25254984784058ab6bc99af3423ad1
Source dataset
uspto-grants-2010_06
Patent number
US07732603B2

Reaction notes

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