Triethylamine → HCID 69512789, compound

HRID 1182276Notes

Reaction equation

HRID 1182276 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)=[CH:5][CH:4]=1.[CH3:16][C:17]([CH3:22])([CH3:21])[C@@H:18]1[O:20][CH2:19]1.C(N(CC)CC)C>C(O)(C)C>[CH3:16][C:17]([CH3:22])([CH3:21])[C@H:18]([OH:20])[CH2:19][N:11]1[CH:12]=[CH:13][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:8][CH:7]=2)=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7005022(2S)-2-(1,1-Dimethylethyl)oxiraneHCID 178506113HCID 178506113, compound

Product 1

HCID 69512789HCID 69512789, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4.11 g (19.4 mmol) of 3-[4-(trifluoromethyl)phenyl]-1H-pyrazole, 2.0 g (19.9 mmol) of (S)-3,3-dimethyl-1,2-epoxybutane, 3.1 mL (22.3 mmol) of triethylamine, and 10 mL of isopropyl alcohol was placed in a sealed tube and heated at 85° C. for 48 h. Solvent was evaporated and the residue was purified by silica gel chromatography eluting with ethyl acetate:hexanes (1:7) to give 2.92 g (49%) of (2S)-3,3-dimethyl-1-{3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}-2-butanol as a pale yellow solid and 0.4 g (7%) of its isomer (2S)-3,3-dimethyl-1-{5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}-2-butanol. Data for (2S)-3,3-dimethyl-1-{3-[4-(tifluoromethyl)phenyl]-1H-pyrazol-1-yl}-2-butanol: 1H-NMR (DMSO-d6): δ 7.96 (d, J 8 Hz, 2H), 7.75 (s, 1H), 7.69 (d, J=8 Hz, 2H), 6.76 (d, J=2 Hz, 1H), 4.86 (d, J=6 Hz, 1H), 4.26 (dd, J=14 Hz, J=2 Hz, 1H), 3.88 (dd, J=14 Hz, J=10 Hz, 1H), 3.45–3.50 (m, 1H), 0.88 (s, 9H); ES-LCMS m/z 313 (M+H). Data for (2S)-3,3-dimethyl-1-{5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}-2-butanol: 1H-NMR (DMSO-d6): δ 7.87 (d, J=8 Hz, 2H), 7.80 (d, J=8 Hz, 2H), 7.52 (d, J=2 Hz, 1H), 6.42 (d, J=2 Hz, 1H), 5.01 (d, J=6 Hz, 1H), 4.10 (dd, J=14 Hz, J=2 Hz, 1H), 3.92 (dd, J=14 Hz, J=10 Hz, 1H), 3.62–3.67 (m, 1H), 0.82 (s, 9H); ES-LCMS m/z 313 (M+H).

Workup

  1. customwas placed in a sealed tube
  2. customSolvent was evaporated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with ethyl acetate:hexanes (1:7)

Sources & evidence

ORD record
ord-e6ba7179568f4dc5a9e19a6716064ca7
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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