Triacetoxyperiodinane → 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde

HRID 607050Notes

Reaction equation

HRID 607050 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH2:30][OH:31])[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[CH:22][C:21]=3[CH:30]=[O:31])[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86628752(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(hydroxymethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 576178812-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(hydroxymethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (510 mg, 1.017 mmol) in CH2Cl2 (20 mL) at 0° C. under N2, was added Dess-Martin periodinane (647 mg, 1.526 mmol) portionwise. The reaction was stirred at 0° C. for 1 h. The reaction was carefully quenched with saturated NaHCO3 and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel to give 2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzaldehyde as a white solid. LCMS calc.=500.1; found=500.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 10.29 (s, 1H); 8.04 (d, J=7.8 Hz, 1H); 7.93 (s, 1H); 7.85 (d, J=8.0 Hz, 1H); 7.83 (s, 1H); 7.82 (s, 2H); 5.77 (d, J=7.9 Hz, 1H); 5.11 (d, J=16.5 Hz, 1H); 4.94 (d, J=16.5 Hz, 1H); 4.23-4.18 (m, 1H); 0.84 (d, J=6.5 Hz, 3H).

Workup

  1. customThe reaction was carefully quenched with saturated NaHCO3
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9a5e075ce4d2465da24026368565c11f
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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