Hydrochloric Acid → 4-(5-Bromoindolin-1-yl)cyclohexanone

HRID 1922515노트

반응식

HRID 1922515 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]1)[CH2:6][CH2:5]2.Cl>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[CH2:6][CH2:5]2

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 585053135-Bromo-1-(1,4-dioxaspiro[4.5]decan-8-yl)indoline

생성물 1

HCID 598070744-(5-Bromoindolin-1-yl)cyclohexanone수율 83.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of compound 4 (4.0 g, 11.83 mmol) in acetone (50 mL) was treated with 10% HCl solution (50 mL) and the resulting mixture was stirred for over night (16 h). Acetone was evaporated, crude was basified with 2 N NaOH solution and product was extracted into CH2Cl2 (3×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4) to obtain compound 5 (2.9 g, 83%) as a solid. 1H NMR (CDCl3) δ 7.15 (d, J=6.6 Hz, 2H), 6.32 (d, J=8.7 Hz, 1H), 3.81 (tt, J=7.2, 23.4 Hz, 1H), 3.37 (t, J=16.8 Hz, 2H), 2.95 (t, J=16.5 Hz, 2H), 2.51-2.41 (m, 4H), 2.18-2.11 (m, 2H), 1.92-1.78 (m, 2H). MS-ESI (m/z, %): 296 (96), 294 (M+, 100), 200 (30).

후처리

  1. customAcetone was evaporated
  2. extractionwas extracted into CH2Cl2 (3×25 mL)
  3. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography on silica gel (ethyl acetate:hexanes, 1:4)

출처 및 근거

ORD 기록
ord-dc6c85701d9e4229b65649a5c22abca5
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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