Potassium Fluoride → HCID 22615112, compound

HRID 843137Notes

Reaction equation

HRID 843137 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[O:13][C:14]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH2:25][CH2:24]3)[C:15]=2[C:16]=1[CH3:17])=O)C.[F-].[K+]>C1COCC1.O.C(OCC)(=O)C>[CH3:17][C:16]1[C:15]2[C:18]([O:22][CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH2:25][CH2:24]3)=[CH:19][CH:20]=[CH:21][C:14]=2[O:13][C:12]=1[CH2:10][OH:9]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 21226445Aluminium lithium hydrideHCID 53974102HCID 53974102, compound

Product 1

HCID 22615112HCID 22615112, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) suspension of LiAlH4 (17 mg) in THF (1 ml) was added a solution of 3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-4-yloxy)-benzofuran-2-carboxylic acid ethyl ester (44 mg), the compound in Example 108, in THF (0.5 ml) and the resulting suspension was stirred at 0° C. for one hour. To the suspension was dropwise added a solution of KF (122 mg) in H2O (100 μl) at 0° C. over five minutes. The suspension was stirred at room temperature for 30 minutes and diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH=10:1 as a developing solvent) to give [3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-4-yloxy)-benzofuran-2-yl]-methanol (33 mg) as a colorless oil. FAB-MS: m/z 353 (MH+); 1H-NMR (CDCl3): δ 2.00 (4H, m), 2.38 (3H, s), 2.42 (2H, m), 2.68 (2H, m), 3.55 (2H, s), 4.51 (1H, m), 4.71 (2H, s), 6.59 (1H, d, J=8 Hz), 7.00 (1H, d, J=8 Hz), 7.13 (1H, t, J=8 Hz), 7.26 (1H, dd, J1=8 Hz, J2=5 Hz), 7.68 (1H, dt, J1=8 Hz, J2=2 Hz), 8.51 (1H, dd, J1=5 Hz, J2=2 Hz), 8.54 (1H, d, J=2 Hz).

Workup

  1. temperatureTo a cooled
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-5ad54983ae6d4b5dad540b990324a7dc
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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