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Pyridine → 4-nitrophenyl (1S)-2,2-dimethyl-1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl}propyl carbonate

HRID 1182303
Notes
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Reaction equation

HRID 1182303 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C@H:3]([OH:14])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6]1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCCl>[C:18](=[O:19])([O:14][C@H:3]([CH2:4][N:5]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6]1)[C:2]([CH3:16])([CH3:15])[CH3:1])[O:20][C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 69513260(2S)-3,3-dimethyl-1-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-butanol

Product 1

HCID 675671294-nitrophenyl (1S)-2,2-dimethyl-1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl}propyl carbonateYield 93.4%

Reagents, catalysts & solvents

1
HCID 111,2-DichloroethaneSolvent

Procedure

To 875.3 mg (3.71 mmol) of (2S)-3,3-dimethyl-1-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-butanol in 12 mL of 1,2-dichloroethane at room temperature was added 746.8 g (3.71 mmol) of 4-nitrophenyl chloroformate. Then, 359.6 μL (4.45 mmol) of pyridine was added and the solution was heated at reflux for 22 h. Upon cooling to room temperature, saturated aqueous sodium bicarbonate was added to the solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:4) to give 1.39 g (93%) of 4-nitrophenyl (1S)-2,2-dimethyl-1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl}propyl carbonate. Rf=0.29 (3:7 ethyl acetate:hexanes); 1H-NMR (300 MHz, DMSO-d6): δ 8.28 (d, J=9 Hz, 2H), 8.07 (s, 1H), 7.31 (d, J=9 Hz, 2H), 6.74 (s, 1H), 4.87 (d, J=8 Hz, 1H), 4.69 (d, J=14 Hz, 1H), 4.42 (dd, J=15 Hz, J=10 Hz, 1H), 1.03 (s, 9H); ES-LCMS m/z 424 (M+H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 22 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-eed69cf2ce2049fb979c123439a83784
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07288541B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes