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

HRID 1751099Notes

Reaction equation

HRID 1751099 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-e9de381326164128ae8416e474185400
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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