Tetrahydrofuran → Methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801253노트

반응식

HRID 1801253 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](/[N:11]=[CH:12]/[C:13]2[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:7][CH:6]=1)=[O:4].[C:29](OCC)(=O)C.[O:35]1[CH2:39][CH2:38][CH2:37]C1>FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH2:19]([O:18][C:16]([C:15]1[CH:14]=[C:13]([CH:12]2[C:38]([CH3:29])([CH3:37])[CH:39]([OH:35])[C:7]3[C:8](=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[NH:11]2)[CH:28]=[CH:27][CH:26]=1)=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 178498127HCID 178498127, 화합물

생성물 1

HCID 67442282Methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate수율 78.9%

시약·촉매·용매 1

HCID 2733939Yttrium trifluoromethanesulfonate촉매

실험 절차

To a solution of (E)-benzyl 3-((4-(methoxycarbonyl)phenylimino)methyl)benzoate (15.0 g, 40.1 mmol, 1.0 eq.), yttrium(III) trifluoromethanesulfonate (0.5 g, 0.8 mmol, 0.02 eq.) in Tetrahydrofuran (85 mL) in a four-necked flask was added Isobutyl aldehyde (3.18 g, 44.2 mmol, 1.1 eq.) via syringe. The reaction mixture was stirred at room temperature under nitrogen overnight. Thin layer chromatography (Petroleum ether:ethyl acetate=6:1) showed the reaction was complete. The reaction mixture was washed with water and the aqueous layer was extracted with ethyl acetate (twice). The organic layers were washed with brine, dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography (Petroleum ether:ethyl acetate=5:1, then 2:1) to afford 14.2 g of methyl 2-(3-(benzyl oxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid, which was used in next step without further purification. Yield: 78.9%. MS (ESI+APCI) M−17=428.1.

후처리

  1. washThe reaction mixture was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate (twice)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography (Petroleum ether

출처 및 근거

ORD 기록
ord-f34d25377ebd4e76989f259135b67a55
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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