Triacetoxyperiodinane → HCID 76694887, compound

HRID 1867259Notes

Reaction equation

HRID 1867259 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]3[C:11]([CH2:23][CH2:24][CH2:25][OH:26])([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12]([C:14](=[O:16])[CH3:15])=[N:13][N:7]3[C:6]=2[CH:27]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:14]([C:12]1[C:11]([CH2:23][CH2:24][CH:25]=[O:26])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:8]2[CH2:9][O:10][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][C:6]=3[N:7]2[N:13]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 68447558HCID 68447558, compound

Product 1

HCID 76694887HCID 76694887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[8-Chloro-3-(3-hydroxypropyl)-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone (4-4; a racemic mixture, 15 mg, 39 μmol) was dissolved in anhydrous CH2Cl2 (2 mL) and was treated with Dess-Martin periodinane (25 mg, 58 μmol) and the resulting cloudy yellow solution was stirred 1.5 h. Upon completion, the cloudy solution was treated with 1 mL sat. sodium thiosulfate/NaHCO3 solution (1:1) and stirred 30 min. The mixture was extracted with EtOAc (3×5 mL), and the combined organics were dried (MgSO4), filtered and concentrated. The crude residue 3-(2-acetyl-8-chloro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal (4-5; a racemic mixture) was carried directly into the next transformation.

Workup

  1. stirringstirred 30 min
  2. extractionThe mixture was extracted with EtOAc (3×5 mL)
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d0f178a0cc9a498096ee78dcb9e84074
Source dataset
uspto-grants-2009_12
Patent number
US07632833B2

Reaction notes

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