Metaperiodic acid → HCID 57659749, compound

HRID 1011605Notes

Reaction equation

HRID 1011605 reaction equation
I(O)(=O)(=O)=[O:2].[CH:6]1([C@@H:9]2[C:16]3[CH:15]=[N:14][NH:13][C:12]=3[CH2:11][N:10]2[S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:8][CH2:7]1>CC#N.[O-2].[Cr+3].[O-2].[O-2].[Cr+3]>[CH:6]1([C@@H:9]2[C:16]3[CH:15]=[N:14][NH:13][C:12]=3[C:11](=[O:2])[N:10]2[S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 25095935HCID 25095935, compound

Product 1

HCID 57659749HCID 57659749, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 165971Chromium oxideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To periodic acid (176 mg, 0.770 mmol) in CH3CN (2 mL) was added chromium(III) oxide (2.1 mg, 0.021 mmol). The reaction was stirred several minutes until it turned fluorescent orange and all solids were dissolved. The reaction was cooled to 0° C. and a solution of (R)-4-cyclopropyl-5-(4-(trifluoromethyl)phenylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole (12) (50 mg, 0.14 mmol) in CH3CN (1 mL) was added. The reaction was stirred for 1 hr until TLC monitoring showed the disappearance of starting material. The reaction was filtered through a plug of Celite and concentrated in vacuo. The residue was taken up in EtOAc (2 mL) and washed with water (2 mL), 5% NaHSO3 (2 mL), brine (2 mL), dried over Na2SO4, and concentrated in vacuo. The resulting crude product was purified via column chromatography using EtOAc/hexane gradients to yield (R)-4-cyclopropyl-5-(4-(trifluoromethyl)phenylsulfonyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (23) (15 mg, 28%) as a white solid.

Workup

  1. dissolutionall solids were dissolved
  2. stirringThe reaction was stirred for 1 hr until TLC monitoring
  3. filtrationThe reaction was filtered through a plug of Celite
  4. concentrationconcentrated in vacuo
  5. washwashed with water (2 mL), 5% NaHSO3 (2 mL), brine (2 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified via column chromatography

Sources & evidence

ORD record
ord-657e56801d054d6aa49bdac769754674
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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