Methyl 3-(2-oxoindolin-3-yl)propanoate → 3-(3-Hydroxypropyl)indolin-2-one

HRID 1751099ノート

反応式

HRID 1751099 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[CH:16]([CH2:17][CH2:18][C:19](OC)=[O:20])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1>O1CCCC1>[OH:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:7]

参加物

4

反応物 2

HCID 14903583Methyl 3-(2-oxoindolin-3-yl)propanoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 122442773-(3-Hydroxypropyl)indolin-2-one収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (0.5M solution in diglyme, 13.8 mL, 6.9 mmol) was added dropwise at 0° C. to methyl 3-(2-oxoindolin-3-yl)propanoate (1.51 g, 6.90 mmol) in tetrahydrofuran (30 mL). The mixture was allowed to warm to room temperature and then quenched with 2N aqueous hydrochloric acid. The reaction was extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (50% ethyl acetate/hexanes) to give product as a white solid (1.13 g, 86%); 1H NMR (DMSO-d6); δ1.38 (m, 2H); 1.85 (m, 2H); 3.32-3.38 (t, J=6.4 Hz, 1H); 4.38 (t, J=5.2 Hz, 1H); 6.80 (d, J=8 Hz, 1H); 6.94 (m, 1H); 7.16 (m, 1H); 7.22 (d, J=7.2 Hz, 1H); 10.3 (s, 2H)

後処理

  1. customquenched with 2N aqueous hydrochloric acid
  2. extractionThe reaction was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by Biotage flash column chromatography (50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-e9de381326164128ae8416e474185400
出典データセット
uspto-grants-2015_10
特許番号
US09156840B2

反応ノート

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