Hydrochloric Acid → 9a-butyl-7-hydroxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7841

반응식

HRID 7841 반응식
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:34]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].CCS.[Al+3].[Cl-].[Cl-].[Cl-].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O.O.O1CCCC1>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]4)=[CH:23][CH:24]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:34])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 219909249a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

생성물 1

HCID 115116099a-butyl-7-hydroxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

An ice-cold solution of 9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)-ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg, 96% weight pure, 0.172 mmol) in anhydrous CH2Cl2 (1.2 mL) was placed under a nitrogen atmosphere and treated with EtSH (0.055 mL, 0.743 mmol). The resulting solution was added by syringe to AlCl3 (115.2 mg, 0.864 mmol) contained in an ice-cold flask and kept under nitrogen. The resulting solution was stirred at 0° C. for 3 minutes, then at room temperature for 35 minutes. The mixture was cooled in an ice bath, treated with 0.5N HCl (1.6 mL) and tetrahydrofuran (1.0 mL), and stirred at 0° C. for 10 minutes. The resulting mixture was diluted with EtOAc (20 mL) and water (15 mL) and stirred while basifying with solid NaHCO3. The layers were separated and the aqueous portion extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to afford 9a-butyl-7-hydroxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a yellow semi-solid.

후처리

  1. customcontained in an ice-cold flask
  2. waitat room temperature for 35 minutes
  3. temperatureThe mixture was cooled in an ice bath
  4. stirringstirred at 0° C. for 10 minutes
  5. stirringstirred
  6. customThe layers were separated
  7. extractionthe aqueous portion extracted with EtOAc
  8. washThe combined organics were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-c98b40057f6544e1a3bf91358949001b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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