tert-Butyl methyl ether → HCID 87158512, compound

HRID 2206931Notes

Reaction equation

HRID 2206931 reaction equation
[Cl:1][C:2]1[C:3]([F:35])=[C:4]([C:9]2([C:31]([F:34])([F:33])[F:32])[CH2:13][CH2:12][N:11]([C:14]3[CH:26]=[CH:25][C:17]([CH2:18][NH:19][C:20]([CH:22]4[CH2:24][CH2:23]4)=[O:21])=[C:16]([C:27]([F:30])([F:29])[F:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N+]([O-])([O-])=[O:37].[NH4+].[Ce].COC(C)(C)C>CN(C)C=O>[Cl:1][C:2]1[C:3]([F:35])=[C:4]([C:9]2([C:31]([F:34])([F:32])[F:33])[CH2:13][CH2:12][N:11]([C:14]3[CH:26]=[CH:25][C:17]([CH2:18][NH:19][C:20]([CH:22]4[CH2:23][CH2:24]4)=[O:21])=[C:16]([C:27]([F:28])([F:29])[F:30])[CH:15]=3)[CH:10]2[OH:37])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 57418452Ammonium cerium-nitrateHCID 87158462HCID 87158462, compound

Product 1

HCID 87158512HCID 87158512, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{4-[3-(3,5-dichloro-2-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-(trifluoro-methyl)benzyl}cyclopropanecarboxamide (0.18 g) was dissolved in N,N-dimethylformamide (5 ml), cooled by using an ice bath, and then stirred. To the solution, a 1 M aqueous solution of cerium ammonium nitrate (IV) (0.72 ml) was added dropwise and stirred in an ice bath for 2 minutes. After that, t-butyl methyl ether was added for dilution and the organic layer was washed with water, an aqueous solution of sodium thiosulfate and saturated brine in that order. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure, and the residue obtained was purified by column chromatography to obtain N-{4-[3-(3,5-dichloro-2-fluorophenyl)-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl]-2-(trifluoromethyl)benzyl}cyclopropanecarboxamide (0.08 g).

Workup

  1. temperaturecooled
  2. stirringstirred in an ice bath for 2 minutes
  3. washthe organic layer was washed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2819cd34da8e4fb2b34813ff1c977ffe
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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