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Hydrochloric Acid → 2-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 1964145
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HRID 1964145 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][CH3:34])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][CH:20]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[C:13]3=[CH:12][C:11]=2[CH:10]=1)[CH3:2].[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][CH3:34])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][CH:20]([CH2:21][C:22]([OH:24])=[O:23])[C:13]3=[CH:12][C:11]=2[CH:10]=1)[CH3:2]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86654874tert-Butyl 2-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 583295752-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid수율 86.3%

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

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온도
70 °C

실험 절차

tert-Butyl 2-(7-(3,4-diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (173.1 mg) was taken up in dioxane (4 mL) and 1.0 M aqueous LiOH (1.11 mL) was added. The reaction was stirred at 70° C. 16 h, and stirred at 80° C. for an additional 5 h. The mixture was cooled to room temperature and poured into a separatory funnel containing EtOAc and 1.0 M HCl. The water layer was removed and the EtOAc layer was washed with water. The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give title compound (131.4 mg). LCMS m/z=410.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.28-1.34 (m, 6H), 2.15-2.26 (m, 1H), 2.54 (dd, J=16.3, 7.9 Hz, 1H), 2.68 (dd, J=16.3, 6.7 Hz, 1H), 2.72-2.82 (m, 1H), 3.53-3.62 (m, 1H), 3.91-4.93 (m, 6H), 4.95 (s, 2H), 6.0 (s, 1H), 6.73 (dd, J=8.7, 2.4 Hz, 1H), 6.90-6.96 (m, 2H), 7.02-7.06 (m, 2H), 7.17 (d, J=9.0 Hz, 1H), 12.3 (bs, 1H).

후처리

  1. stirring16 h, and stirred at 80° C. for an additional 5 h
  2. temperatureThe mixture was cooled to room temperature
  3. additionpoured into a separatory funnel
  4. customThe water layer was removed
  5. washthe EtOAc layer was washed with water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9b3a362e3a0c4f6fb90d22236eecf88a
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415484B2

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