Dimethylformamide → 6-Hydroxy-8-(5-phenyl-2-pentyloxy)-3a,4-dihydro(2H,3H)-pyrrolo[1,2-a]quinolin-1,5-dione

HRID 1632571노트

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HRID 1632571 반응식
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH2:5][CH:6]1[CH2:15][CH2:14][C:13](=[O:16])[N:7]12.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:34]([CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:35])(=O)=O>C(OCC)(=O)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:34]([CH2:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:35])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:17])[CH2:5][CH:6]1[CH2:15][CH2:14][C:13](=[O:16])[N:7]12

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 11430Potassium Carbonate2회HCID 128783865-Phenyl-2-pentanol mesylate2회HCID 133667053a,4-Dihydro-6,8-dihydroxy-2H,3H-pyrrolo[1,2-a]quinoline-1,5-dione

생성물 1

HCID 133667066-Hydroxy-8-(5-phenyl-2-pentyloxy)-3a,4-dihydro(2H,3H)-pyrrolo[1,2-a]quinolin-1,5-dione

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

Under anhydrous conditions and in a nitrogen atmosphere, 70 g. (0.30 mole) 6,8-dihydroxy-3a,4-dihydro-(2H,3H)-pyrrolo[1,2-a]quinolin-1,5-dione was dissolved in 750 ml. dimethylformamide by warming to 60° C. To the resulting deep red solution was added 51.6 g. (0.675 mole) potassium carbonate. The mixture was heated to 70° C., a solution of 2-methylsulfonyloxy-5-phenylpentane in 250 ml. dimethylformamide was added in a fast stream, and heated at 75°-80° C. for 12 hours. Additional portions of 2-methylsulfonyloxy-5-phenylpentane (5.3 g.) and potassium carbonate (3.8 g.) and heating continued at 75°-80° C. for two hours. The mixture was poured over a mixture (one liter each) ethyl acetate and ice and, after shaking in a separtory funnel, the layers were separated. The aqueous phase was extracted with 5×1000 ml. ethyl acetate. The combined organic layers were washed with 3×4 liters water, 3×2 liters of 0.5N hydrochloric acid, dried (MgSO4) and concentrated to a volume of about 2.5 liters. Upon cooling, the precipitated product which formed was collected: 9.0 g., M.P. 151°-153° C. The mother liquor was concentrated to half volume, cooled, and a second crop, 34.2 g., M.P. 148°-151° C., was collected. Total yield by crystallization: 52.2 g. This material was shown to be primarily a single diastereomer, designated as "Diastereomer B." Upon recrystallization from ethyl acetate, colorless crystals were obtained, M.P. 159°-161° C. This was found to be about 90% diastereomer B. 1H--NMR (CDCl3) ppm (delta): 1.33 (d, 3H, J=6 Hz).

후처리

  1. additionTo the resulting deep red solution was added 51.6 g
  2. temperatureheated at 75°-80° C. for 12 hours
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with 5×1000 ml
  5. washThe combined organic layers were washed with 3×4 liters water, 3×2 liters of 0.5N hydrochloric acid
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a volume of about 2.5 liters
  8. temperatureUpon cooling
  9. customthe precipitated product which formed
  10. customwas collected
  11. concentrationThe mother liquor was concentrated to half volume
  12. temperaturecooled
  13. custom, M.P. 148°-151° C., was collected
  14. customTotal yield by crystallization
  15. custom" Upon recrystallization from ethyl acetate
  16. customcolorless crystals were obtained

출처 및 근거

ORD 기록
ord-219977dead114794900f8f7fc7db5a80
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04476131

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