6-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol → 9-Hydroxy-9-[5(2-naphthyl)-1H-imidazol-2-yl]nonan-3-one

HRID 913060Notes

Reaction equation

HRID 913060 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[N:16](COCC[Si](C)(C)C)[CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[N:19]=2)[OH:14])OCC[O:4]1)[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:14][CH:13]([C:15]1[NH:19][C:18]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[CH:17][N:16]=1)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:3](=[O:4])[CH2:1][CH3:2]

Participants

3

Reactant 1

HCID 673820876-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-ol

Product 1

HCID 673818489-Hydroxy-9-[5(2-naphthyl)-1H-imidazol-2-yl]nonan-3-one

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The alcohol F2 was dissolved in TFA/DCM (1:1) and stirred for 4 hr at RT. The reaction was quenched with sat. aq. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and solvent was removed under reduced pressure. The crude product was purified by flash chromatography, using EtOAc/petroleum ether as eluents and the product was obtained as a white solid. 1H NMR (300 MHz, DMSO) δ: 8.30 (1H, s), 7.97-7.75 (6H, m), 7.58-7.41 (2H, m), 5.81 (1H, br s), 4.75 (1H, m), 2.37 (4H, m), 1.80 (2H, m), 1.51-1.19 (6H, m), 0.88 (3H, t, J=7.3 Hz). MS (ES) C22H26N2O2 requires: 350, found: 351 (M+H)+.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3 solution
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4) and solvent
  4. customwas removed under reduced pressure
  5. customThe crude product was purified by flash chromatography
  6. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-2dfbe3388f284d0faf1cae0f2e8ef480
Source dataset
uspto-grants-2011_09
Patent number
US08026265B2

Reaction notes

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