Potassium Sodium Tartrate → HCID 58269932, 화합물

HRID 602541노트

반응식

HRID 602541 반응식
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([C:16]3[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:24][CH3:25])[CH:14]=2)[N:9]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:8]=1)C.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[CH2:22]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:24][CH3:25])[C:16]=1[C:13]1[CH:14]=[C:15]2[C:7]([CH2:6][CH2:5][CH2:4][OH:3])=[CH:8][N:9]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)[C:10]2=[CH:11][N:12]=1)[CH3:23]

참가 물질

5

반응물 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67152479HCID 67152479, 화합물

생성물 1

HCID 58269932HCID 58269932, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 3-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-propionic acid ethyl ester (220 mg, 0.47 mmol, prepared by the procedure described in Example 11, Step 5) in DCM (4 mL) at −78° C., DIBAL (1M solution in toluene, 2.35 mL, 2.3 mmol) is added, and the mixture is stirred at −78° C. for 3 h. Reaction is warmed up to room temperature, and a saturated aqueous Rochelle's salt solution (6 mL) is carefully added. Stirring is continued for another 1 hour. The organic layer is separated, and the aqueous phase is extracted with DCM. The combined organic solutions are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue affords 3-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-propan-1-ol as a colorless oil. 1H NMR: (CDCl3) 8.97 (s, 1H), 7.49 (s, 1H), 7.48 (d, J=12 Hz, 2H), 7.42 (d, J=10 Hz, 2H), 7.32 (s, 1H), 7.27 (t, J=10 Hz, 1H), 7.15 (d, 12 Hz, 2H), 3.76 (t, J=6 Hz, 2H), 3.01 (m, 1H), 2.89 (t, J=6 Hz, 2H), 2.35 (m, 4H), 2.01 (m, 2H), 1.33 (d, J=10 Hz, 6H), 1.073 (t, J=10 Hz, 6H); LCMS m/z 427.32 (2.32 min).

후처리

  1. customat −78° C.
  2. customReaction
  3. temperatureis warmed up to room temperature
  4. stirringStirring
  5. waitis continued for another 1 hour
  6. customThe organic layer is separated
  7. extractionthe aqueous phase is extracted with DCM
  8. washThe combined organic solutions are washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-529f02479a5c49ed99ff8aaf37c3b581
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906528B2

반응 노트

불러오는 중…