Acetonitrile → HCID 87158603, compound

HRID 2206903Notes

Reaction equation

HRID 2206903 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[C:10]([Br:38])=[N:11][C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[CH2:16]2)=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C(#N)C.[N+]([O-])([O-])=[O:44].[NH4+].[Ce]>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[C:10]([Br:38])=[N:11][C:12]([N:15]2[CH2:19][CH2:18][C:17]([C:24]3[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[C:26]([C:34]([F:37])([F:35])[F:36])[CH:25]=3)([C:20]([F:22])([F:23])[F:21])[CH:16]2[OH:44])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 57418452Ammonium cerium-nitrateHCID 87160558HCID 87160558, compound

Product 1

HCID 87158603HCID 87158603, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of t-butyl[(6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-2-bromopyridin-3-yl)methyl]carbamate (0.5 g) and acetonitrile (30 ml), which had been stirred in ice water bath, a 1 M aqueous solution of cerium ammonium nitrate (IV) (1.6 ml) was added, stirred approximately for 10 minutes and the reaction mixture was diluted with ethyl acetate. After that, the mixture was washed with an aqueous solution of sodium thiosulfate and then an aqueous saturated brine solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography to obtain t-butyl[(6-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-2-bromopyridin-3-yl)methyl]carbamate (0.35 g).

Workup

  1. washAfter that, the mixture was washed with an aqueous solution of sodium thiosulfate
  2. dry with materialan aqueous saturated brine solution and dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-80ab7ffd96e34e8d9184c3d9879364ba
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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