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

HRID 2045532ノート

反応式

HRID 2045532 の反応式
[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

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 178498127HCID 178498127、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 2733939Yttrium trifluoromethanesulfonate触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e06fde9ba774a00beaac504ef89defd
出典データセット
uspto-grants-2013_11
特許番号
US08586747B2

反応ノート

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