Potassium Sodium Tartrate → HCID 58269932、化合物

HRID 472039ノート

反応式

HRID 472039 の反応式
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]

参加物

5

反応物 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67152479HCID 67152479、化合物

生成物 1

HCID 58269932HCID 58269932、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c64ef5e4ec641f7af8dd150c4bea39c
出典データセット
uspto-grants-2014_01
特許番号
US08633193B2

反応ノート

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