Sodium cyanoborohydride → (2R,3R)-2-(2,4-difluorophenyl)-3-((1-(2-fluorophenyl)piperidin-4-yl)amino)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1430086노트

반응식

HRID 1430086 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1.[NH2:15][C@H:16]([CH3:33])[C@:17]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[F:32])([OH:24])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C([BH3-])#N.[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C@:17]([OH:24])([C@H:16]([NH:15][CH:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][CH2:10]1)[CH3:33])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 10967497(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-olHCID 111168931-(2-Fluorophenyl)piperidin-4-one

생성물 1

HCID 53357279(2R,3R)-2-(2,4-difluorophenyl)-3-((1-(2-fluorophenyl)piperidin-4-yl)amino)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol수율 44%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매

실험 절차

To a solution of 1-(2-fluorophenyl)piperidin-4-one (36.0 mg, 0.19 mmol) in anhydrous ethanol (1 mL) was added (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (50.0 mg, 0.19 mmol). While being stirred, the reaction solution was mixed at room temperature for four hrs with titanium (IV) isopropoxide (0.06 mL, 0.21 mmol) and then at room temperature for 18 hrs with sodium cyanoborohydride (35.0 mg, 0.56 mmol). The reaction was terminated by adding distilled water, after which the reaction mixture was concentrated by evaporation at reduced pressure and extracted with ethyl acetate to give an organic solvent layer. This organic layer was dried over anhydrous magnesium sulfate and purified by silica gel chromatography to afford the title compound (yield 44%).

후처리

  1. customThe reaction was terminated
  2. additionby adding
  3. distillationdistilled water
  4. concentrationafter which the reaction mixture was concentrated by evaporation at reduced pressure
  5. extractionextracted with ethyl acetate
  6. customto give an organic solvent layer
  7. dry with materialThis organic layer was dried over anhydrous magnesium sulfate
  8. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ba8912afa48542edbf0779fbc4811086
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940768B2

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