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

HRID 2363030노트

반응식

HRID 2363030 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 122442773-(3-Hydroxypropyl)indolin-2-one수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 weashed 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)

후처리

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

출처 및 근거

ORD 기록
ord-605fdc8010df452f90bec215655ee48c
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691836B2

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