Acetic Acid → tert-butyl 4-(2-(1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2172314Notes

Reaction equation

HRID 2172314 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=3[C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(O)(=O)C>CO.[Pt](=O)=O>[CH2:1]1[C:10]2[C:5](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][C:12]=3[C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89813602tert-butyl 4-(2-(isoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89815601tert-butyl 4-(2-(1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylateYield 83.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(2-(isoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (9.80 g, 21.56 mmol) in 50 mL MeOH was treated with acetic acid (1.234 ml, 21.56 mmol) and platinum(IV) oxide (Sigma-Aldrich, St. Louis, Mo., 0.979 g, 4.31 mmol) and was placed under 45 psi (4559.6 kpa) H2 overnight. The reaction mixture was filtered through a plug of diatomaceous earth and concentrated. The resulting residue was taken up in DCM, was washed with saturated NaHCO3 solution, the organics dried over MgSO4 and concentrated yielding tert-butyl 4-(2-(1,2,3,4-tetrahydroisoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (8.21 g, 17.91 mmol).

Workup

  1. customwas placed under 45 psi (4559.6 kpa) H2 overnight
  2. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  3. concentrationconcentrated
  4. washwas washed with saturated NaHCO3 solution
  5. dry with materialthe organics dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-558e8924bbc843b5ac1e1c3d1ac6e06d
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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