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

HRID 2172289노트

반응식

HRID 2172289 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 887Methanol용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-31932ae48e914789b89895cc656a7985
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051311B2

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