Hydrochloric Acid → 4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1095144노트

반응식

HRID 1095144 반응식
Cl[C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:42])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3C3C=C(Cl)C=CC=3OC3CCC4(OCCO4)CC3)[C:5]2=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>O1CCCC1.O>[Cl:22][C:18]1[CH:17]=[C:16]([CH:15]2[CH2:14][C:13](=[O:23])[NH:12][CH2:11][C:10]32[C:5]2[C:6](=[CH:7][CH:2]=[CH:3][CH:4]=2)[NH:8][C:9]3=[O:42])[CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866317946-chloro-2'-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

생성물 1

HCID 686290234'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione수율 95.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.2 g, 0.32 mmol) in tetrahydrofuran (15 mL) and water (1 mL) was added aqueous HCl (2 N, 1 mL). The reaction mixture was stirred at room temperature for 1 h, then neutralized to “pH” 7 by aqueous NaHCO3 solution. The mixture was then extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give racemic(2′R, 3R, 4′S)-6-chloro-2′-[5-chloro-2-cyclohexyloxy)-phenyl]-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.1 g, 54%)

후처리

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

출처 및 근거

ORD 기록
ord-2f3bd0262624468aa4962bf99ea2373b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134001B2

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