Isopropanol → HCID 68858815, compound

HRID 2102690Notes

Reaction equation

HRID 2102690 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12](N1CCCC(=O)C1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[CH3:31]C(O)C>>[C:15]([O:14][C:12]([CH:30]1[CH2:29][CH2:28][C:27]([CH:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])=[CH:31][NH:26]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 68858815HCID 68858815, compound

Conditions

Temperature
90 °C

Procedure

A suspension of 6-chlorooxindole (1.91 g, 11.4 mmol) (Cresent Chem), 1-BOC-3-piperidone (2.5 g, 12.5 mmol) (Martix Scientific), and pyrrolidine (0.1 g, 1.14 mmol) (Aldrich) in 2-propanol (30 mL) was heated at 90° C. for 2 days. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted repeatedly with ethyl acetate. The organic layer was separated, combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-dichloromethane, 1:9, V/V) to give rac-5-[6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-2H-pyridine-carboxylic acid tert-butyl ester as a brown solid. (Yield 2.6 g, 67%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted repeatedly with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (ethyl acetate-dichloromethane, 1:9, V/V)

Sources & evidence

ORD record
ord-37ede13962de4ce4859bdb1fff1b591f
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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