Isopropanol → HCID 68858815, compound

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

Reactant 4

HCID 3776Isopropanol

HCID 31268Pyrrolidine

HCID 7363446-Chloro-1,3-dihydroindol-2-one

HCID 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%).