Sodium Sulfite → N-{[6-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methyl}cyclopropanecarboxamide

HRID 2206920Notes

Reaction equation

[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C:13]2([C:35]([F:38])([F:37])[F:36])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([CH:28]4[CH2:30][CH2:29]4)=[O:27])=[C:20]([C:31]([F:34])([F:33])[F:32])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N+]([O-])([O-])=[O:42].[NH4+].[Ce].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([C:13]2([C:35]([F:36])([F:37])[F:38])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([CH:28]4[CH2:30][CH2:29]4)=[O:27])=[C:20]([C:31]([F:32])([F:33])[F:34])[CH:19]=3)[CH:14]2[OH:42])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-{[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl-}-4-(trifluoro-methyl)pyridin-3-yl]methyl}cyclopropanecarboxamide (0.15 g) was dissolved in acetonitrile (3 ml) and to the solution was added cerium ammonium nitrate (IV) (1 M aqueous solution, 0.51 ml) at 0° C. After stirring at 0° C. for 3 hours, an aqueous solution of sodium sulfite was added, extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. The target compound (0.12 g) was obtained by purification with silica gel column chromatography.

Workup

extractionextracted with ethyl acetate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f8f9cacdf9fb4e1db41272e9bb36493b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

Loading…