Acetic Acid → HCID 90417432, compound

HRID 588276Notes

Reaction equation

HRID 588276 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH2:3][CH2:2]1.[O:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C(O)(=O)C>C1COCC1.CO>[O:17]1[CH2:22][CH2:21][CH:20]([N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10]4)[CH2:5][CH2:6]2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 68798350HCID 68798350, compound

Product 1

HCID 90417432HCID 90417432, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(piperidin-4-yl)indolin-2-one (64.6 mg, 0.299 mmol) in THF (1.5 ml) and MeOH (3 ml) were added dihydro-2H-pyran-4 (3H)-one (0.132 ml, 1.34 mmol), acetic acid (0.170 ml, 29.5 mmol) and NaBH3(CN) (61.6 mg, 0.931 mmol). After stirring at room temperature for 4 days, the reaction mixture was concentrated. The residue was diluted with sat. NaHCO3 aq. and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give 5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)indolin-2-one (84.9 mg, 95%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was diluted with sat. NaHCO3 aq.
  3. extractionextracted with CHCl3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-df517b7bb95f49938a0cd67c205342c6
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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