Diisopropylethylamine → 6-chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-1'-methyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-1′-methyl-2,6′-dioxospiro[indole-3,3′-piperidine]-1-ethanol (0.09 g, 0.175 mmol) prepared in example 56b in methanol (10 mL) was added N,N′-diisopropylethylamine (2 mL, 11.1 mmol) and the crude was refluxed for 1 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was separated, and concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:2) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-1′-methylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.06 g, 70.6%).

1. temperaturethe crude was refluxed for 1 h
2. concentrationThe reaction mixture was concentrated
3. customthe residue was partitioned between ethyl acetate and water
4. customThe organic layer was separated
5. concentrationconcentrated
6. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:2)

ORD record

ord-dc8c4527ccfc493ebdec3f7690b30232

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495007B2