Potassium Fluoride → [3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol

HRID 843139

反応式

HRID 843139 の反応式
[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][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH2:25]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][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH2:25]3)=[CH:19][CH:20]=[CH:21][C:14]=2[O:13][C:12]=1[CH2:10][OH:9]

参加物

7

反応物 3

HCID 522689Potassium FluorideHCID 21226445Aluminium lithium hydrideHCID 544265053-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-carboxylic acid ethyl ester

生成物 1

HCID 54356540[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol収率 98.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a cooled (0° C.) suspension of LiAlH4 (223 mg) in THF (30 ml) was dropwise added a solution of 3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-carboxylic acid ethyl ester (600 mg), the compound in Example 111, in THF (20 ml) and the resulting suspension was stirred at 0° C. for one hour. To the suspension was dropwise added a solution of KF (1 g) in H2O (1.2 ml) at 0° C. over 15 minutes. The suspension was stirred at room temperature for 30 minutes, diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to give [3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol (532 mg) as a colorless oil. FAB-MS: m/z 367 (MH+); 1H-NMR (CDCl3): δ 1.13-2.25 (7H, m), 2.17 (3H, s), 2.81 (1H, br d, J=11 Hz), 2.93 (1H, br d, J=11 Hz), 3.42 (1H, d, J=13 Hz), 3.56 (1H, d, J=13 Hz), 3.84 (1H, dd, J1=9 Hz, J2=8 Hz), 3.96 (1H, dd, J1=9 Hz, J2=5 Hz), 4.68 (2H, s), 6.54(1H, d, J=8 Hz), 7.00 (1H, d, J=8 Hz, 7.13 (1H, t, J=8 Hz), 7.19 (1H, dd, J1=8 Hz, J2=5 Hz), 7.66 (1H, dt, J1=8 Hz, J2=2 Hz), 8.47 (2H, br s).

後処理

  1. temperatureTo a cooled
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated

出典と根拠

ORDレコード
ord-6be850a281474018affcfb64bc1afe72
出典データセット
uspto-grants-2002_04
特許番号
US06376491B1

関連ノート

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