Hydrochloric Acid → methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride

HRID 508571

反応式

HRID 508571 の反応式
COC1C=CC(C[N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=3)[CH2:9]2)=CC=1.[ClH:23]>CO.[OH-].[OH-].[Pd+2]>[ClH:23].[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2)[CH2:16][NH:8]1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 58147238Methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate

生成物 1

HCID 19828495methyl 2,3-dihydro-1H-isoindole-5-carboxylate hydrochloride収率 2,242.3%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒2 回HCID 887Methanol溶媒

実験手順

To a mixture of methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate (0.82 g, 2.76 mmol) and 20% palladium hydroxide on carbon (0.194 g, 0.276 mmol) in methanol (25 mL) was added concentrated HCl (0.41 mL, 0.11 mmol). The mixture was degassed and stirred under a balloon atmosphere of H2 for two days. Additional 20% palladium hydroxide on carbon (0.08 g, 0.11 mmol) was then added and the reaction was continued for an additional day. The insolubles were removed via filtration through Clite and the solution was concentrated. Further drying under vacuum afforded a white powder (0.527 g, 91%). LCMS: (FA) ES+ 179. 1H NMR (d6-DMSO, 400 MHz) δ 9.71 (br s, 2H), 8.01 (s, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.7 Hz 2H), 4.56 (d, J=6.0 Hz, 4H), 3.87 (s, 3H).

後処理

  1. customThe mixture was degassed
  2. waitthe reaction was continued for an additional day
  3. customThe insolubles were removed via filtration through Clite
  4. concentrationthe solution was concentrated
  5. customFurther drying under vacuum

出典と根拠

ORDレコード
ord-29d8c84632db486f9946cff7b9c082d5
出典データセット
uspto-grants-2015_08
特許番号
US09096518B2

関連ノート

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