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

HRID 251607Notes

Reaction equation

HRID 251607 reaction equation
[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

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66994240HCID 66994240, compoundHCID 178478989HCID 178478989, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-68b2cb61eeff4bc6b75f584fdbc6208d
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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