Methanol → 6-chloro-2'-(3-chlorophenyl)-4'-phenyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Temperatur

140 °C

To a solution of 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 1c in toluene (30 mL) was added E/Z-3-benzylidene-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester prepared in Example 12b (0.4 g, 1.22 mmol). The reaction mixture was stirred under nitrogen in a sealed tube at 140° C. for 1 h. After the solution was cooled to room temperature, methanol (40 mL) was added. The reaction mixture was filtered through a short pad of celite gel and washed with ethyl acetate. The filtrate was concentrated. The residue was dissolved in methanol (30 mL) and 1N of NaOH solution (5 mL, 5 mmol) was added. The reaction mixture was stirred at room temperature for 0.5 h, then the mixture was concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:4) to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-phenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a yellow oil (Yield 0.5 g, 100%).

1. temperatureAfter the solution was cooled to room temperature
2. filtrationThe reaction mixture was filtered through a short pad of celite gel
3. washwashed with ethyl acetate
4. concentrationThe filtrate was concentrated
5. dissolutionThe residue was dissolved in methanol (30 mL)
6. stirringThe reaction mixture was stirred at room temperature for 0.5 h
7. concentrationthe mixture was concentrated
8. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:4)

ORD-Eintrag

ord-30094670c3f1479b917cb712f59b89b0

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07495007B2