Ammonium Chloride → Cyclopentyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

HRID 251607

反応式

HRID 251607 の反応式
[CH:1]1([Mg]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11](=O)[C:12]1[C:17]([O:18][CH2:19][CH3:20])=[CH:16][C:15]([C:21]2[C:26]([CH2:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:29][CH3:30])=[N:14][CH:13]=1)C.[Cl-].[NH4+]>CCOCC>[CH:1]1([CH:11]([C:12]2[CH:13]=[N:14][C:15]([C:21]3[C:26]([CH2:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:29][CH3:30])=[CH:16][C:17]=2[O:18][CH2:19][CH3:20])[OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 66994240HCID 66994240、化合物HCID 178478989HCID 178478989、化合物

生成物 1

HCID 59678238Cyclopentyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Cyclopentyl magnesium chloride solution (2 M in THF, 2 mL, 4 mmol) is slowly added to a solution of 6-(2,6-diethyl-phenyl)-4-ethoxy-nicotinic acid ethyl ester (prepared by a route analogous to that given in Example 2) (163 mg, 0.5 mmol) in ether (5 mL) at 0° C. The mixture is stirred at room temperature for 30 minutes. Saturated ammonium chloride solution (2 mL) is added and the organic solution is separated. The organic layer is separated and dried over anhydrous Na2SO4. The solvents are removed in vacuo and the crude is purified with PTLC (hexanes/EtOAc 3:1) to give cyclopentyl-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-methanol. 1H NMR: (CDCl3) 8.44 (s, 1H), 7.28 (t, 1H), 7.12 (d, 2H), 6.74 (S, 1H), 4.61 (t, 1H), 4.06 (q, 2H), 2.29 (m, 4H), 1.92 (m, 1H), 1.47 (m, 10H), 1.21 (m, 1H), 1.02 (m, 6H).

後処理

  1. customprepared by a route analogous to
  2. customat 0° C
  3. customthe organic solution is separated
  4. customThe organic layer is separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvents are removed in vacuo
  7. customthe crude is purified with PTLC (hexanes/EtOAc 3:1)

出典と根拠

ORDレコード
ord-68b2cb61eeff4bc6b75f584fdbc6208d
出典データセット
uspto-grants-2011_01
特許番号
US07863454B2

関連ノート

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