Acetonitrile → HCID 69064282, compound

HRID 1436931Notes

Reaction equation

HRID 1436931 reaction equation
[CH3:1][CH:2]([NH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12]C(C)(C)C)=[O:11])[CH2:6]1)[CH3:3].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:20]=1[CH2:21]Br.[C:30](=[O:33])([O-:32])[O-].[K+].[K+].[C:36](#N)[CH3:37]>C(OCC)(=O)C>[C:10]([OH:12])(=[O:11])/[CH:36]=[CH:37]/[C:30]([OH:32])=[O:33].[CH3:3][CH:2]([N:4]([CH2:21][C:20]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:19]=1[C:18]([F:28])([F:17])[F:29])[C@H:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)[CH3:1]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27375785-Fluoro-2-(trifluoromethyl)benzyl bromideHCID 53346612tert-Butyl (3S)-3-[(propan-2-yl)amino]pyrrolidine-1-carboxylate

Product 1

HCID 69064282HCID 69064282, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethylethyl (3S)-3-[(1-methylethyl)amino]pyrrolidine-1-carboxylate (0.34 g, 1.5 mmol) and 2-(trifluoromethyl)-5-fluorobenzyl bromide (0.58 g, 2.25 mmol) in acetonitrile (5 mL) was heated at reflux with anhydrous potassium carbonate (0.41 g, 3 mmol) for 24 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with water. The organic extracts were washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (0:100 to 10:90), to give the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give an oil
  8. customThis was purified by flash chromatography on silica
  9. washeluting with ethyl acetate/cyclohexane (0:100 to 10:90)

Sources & evidence

ORD record
ord-548bddb55514412eb9b58a507f2fe27a
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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