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

HRID 2172289ノート

反応式

HRID 2172289 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 887Methanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-31932ae48e914789b89895cc656a7985
出典データセット
uspto-grants-2015_06
特許番号
US09051311B2

反応ノート

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