(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone → (2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)pyrrolidin-1-yl]methanone

HRID 551827Notes

Reaction equation

HRID 551827 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[C:25]([F:28])([F:27])[F:26])[CH2:14]2)=[O:12])[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[C:25]([F:26])([F:28])[F:27])[CH2:14]2)=[O:12])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67187504(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone

Product 1

HCID 24853024(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)pyrrolidin-1-yl]methanoneYield 213.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.07 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone in 3.57 ml of methanol is hydrogenated in an H-Cube device under hydrogen at atmospheric pressure with a cartridge of 100 mg of 10% palladium-on-charcoal. After concentrating to dryness, the crude reaction product obtained is chromatographed on silica gel, elution being carried out with a mixture of 5% of ethyl acetate in dichloromethane. 0.15 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)pyrrolidin-1-yl]methanone is obtained.

Workup

  1. concentrationAfter concentrating to dryness
  2. customthe crude reaction product
  3. customobtained
  4. customis chromatographed on silica gel, elution
  5. additionbeing carried out with a mixture of 5% of ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-e1690578beb547acb6cb2b5225a50a07
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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