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

HRID 2172289Notes

Reaction equation

HRID 2172289 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 (0.979 g, 4.31 mmol) and was placed under 45 psi (4459.6 kpa) H2 overnight. LC/MS showed exclusively product, so the reaction mixture was filtered through a plug of diatomaceous earth and concentrated. The resulting residue was taken up in DCM and was washed with saturated NaHCO3 solution. The organics were 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). [M+H]+=459.0

Workup

  1. customwas placed under 45 psi (4459.6 kpa) H2 overnight
  2. filtrationso the reaction mixture was filtered through a plug of diatomaceous earth
  3. concentrationconcentrated
  4. washwas washed with saturated NaHCO3 solution
  5. dry with materialThe organics were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31932ae48e914789b89895cc656a7985
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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