Sodium periodate → 9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde

HRID 1506428Notes

Reaction equation

HRID 1506428 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]23[C:34]4[CH:33]=[CH:32][C:31]([CH:35]([OH:38])CO)=[CH:30][C:29]=4[O:28][CH2:27][CH:8]2[C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]=2[C:23]([F:26])([F:25])[F:24])=[N:10][O:11]3)[CH2:3][CH2:2]1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O>[O:1]1[CH2:2][CH2:3][N:4]([C:7]23[C:34]4[CH:33]=[CH:32][C:31]([CH:35]=[O:38])=[CH:30][C:29]=4[O:28][CH2:27][CH:8]2[C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:13]=2[C:23]([F:25])([F:26])[F:24])=[N:10][O:11]3)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 671683261-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol

Product 1

HCID 866699039b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a homogeneous solution of 1-(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)ethane-1,2-diol (Preparation 60E, 0.074 g, 0.139 mmol) in a mixture of THF (2.0 mL) and water (0.13 mL) at room temperature was added sodium periodate (0.045 g, 0.209 mmol). The reaction mixture was stirred for 60 min. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate, washed with water, and washed with brine. The organic layer was collected, and the combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford a quantitative yield of 9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazole-7-carbaldehyde as a yellow oil. The product had an HPLC ret. time=3.02 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=499.9.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. washwashed with brine
  5. customThe organic layer was collected
  6. extractionthe combined aqueous layers were extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a7679cd5f0e348989500e4bad0efc370
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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