Methyl iodide → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-1'-methyl-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (0.25 g, 0.45 mmol) in N,N-dimethyl-formamide (20 mL) at 0° C. was added LiH (90 mg, 11.2 mmol) (Aldrich), followed by the addition of iodomethane (0.39 g, 2.74 mmol). The reaction mixture was warmed up to room temperature and stirred at room temperature for 3 h. The mixture was diluted with ethyl acetate, and then washed with saturated NH4Cl solution. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over MgSO4. The solvent was removed and the residue was purified by chromatography (EtOAc:hexanes=1:2) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-1′-methyl-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (Yield 0.20 g, 77%).

1. washwashed with saturated NH4Cl solution
2. extractionThe aqueous layer was extracted with ethyl acetate
3. dry with materialthe combined organic layer was dried over MgSO4
4. customThe solvent was removed
5. customthe residue was purified by chromatography (EtOAc:hexanes=1:2)

ORD 기록

ord-db94ed3c1f1b4435b652a2906ff66ccb

출처 데이터셋

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07495007B2