2-(6-Methoxy-2-naphthyl)propionic acid → 1-[4-(3-Trifluoromethylphenyl)-1,2,3,6-tetrahydropyrid-1-yl]-1-oxo-2-(6-methoxy-naphth-2-yl)propane

HRID 53226

Reaction equation

HRID 53226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=O)[CH:7]=[CH:6]2.C(N(CC)CC)C.Cl.[F:26][C:27]([F:41])([F:40])[C:28]1[CH:29]=[C:30]([C:34]2[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=2)[CH:31]=[CH:32][CH:33]=1.C(OCC)(=O)C>C(Cl)Cl>[F:41][C:27]([F:26])([F:40])[C:28]1[CH:29]=[C:30]([C:34]2[CH2:39][CH2:38][N:37]([C:14](=[O:16])[CH:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=3)[CH3:17])[CH2:36][CH:35]=2)[CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 234359914-(3-(Trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 151568771-[4-(3-Trifluoromethylphenyl)-1,2,3,6-tetrahydropyrid-1-yl]-1-oxo-2-(6-methoxy-naphth-2-yl)propaneYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-methoxy-α-methyl-2-naphthylacetic acid (3.5 g, 0.015 mol), triethylamine (4.3 ml, 0.03 mol), 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride (3.9 g, 0.015 mol), and benzotriazolyl-N-oxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) (6 g, 0.015 mol) in methylene chloride (40 ml) is stirred at room temperature for 4 hours. Ethyl acetate (150 ml) is then added thereto and the mixture is washed in sequence with water, 10% NaHCO3, water, 1N HCl, and water. The reaction mixture is then filtered over silica and concentrated to dryness affording 1-[4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyrid-1-yl]-1-oxo-2-(6-methoxy-naphth-2-yl)propane (4 g) as a thick oil.

Workup

  1. washthe mixture is washed in sequence with water, 10% NaHCO3, water, 1N HCl, and water
  2. filtrationThe reaction mixture is then filtered over silica
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cceee2960e2a485cba2374e201abc3ac
Source dataset
uspto-grants-1997_04
Patent number
US05618822

Linked notes

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