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

HRID 251607

반응식

HRID 251607 반응식
[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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 66994240HCID 66994240, 화합물HCID 178478989HCID 178478989, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-68b2cb61eeff4bc6b75f584fdbc6208d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863454B2

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