Phenylpropanolamine → (1R,2S)-1-[(1-isopropyl-1H-indazol-5-yl)oxy]-1-phenylpropan-2-amine

HRID 1098919

반응식

HRID 1098919 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[CH:5]2.[NH2:14][C@@H:15]([CH3:24])[C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC.[Cu]I>[CH:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([O:17][C@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:15]([NH2:14])[CH3:24])=[CH:10][CH:9]=2)[CH:5]=[N:6]1)([CH3:13])[CH3:12]

참가 물질

6

반응물 3

HCID 10297PhenylpropanolamineHCID 10796Cesium carbonateHCID 593398645-iodo-1-isopropyl-1H-indazole

생성물 1

HCID 59339639(1R,2S)-1-[(1-isopropyl-1H-indazol-5-yl)oxy]-1-phenylpropan-2-amine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8008Butyronitrile용매

반응 조건

온도
125 °C

실험 절차

A mixture of 5-iodo-1-isopropyl-1H-indazole (129c, 461 mg, 1.26 mmol), (1R,2S)-2-amino-1-phenylpropan-1-ol (286 mg, 1.89 mmol), copper (I) iodide (25 mg, 130 μmol), and cesium carbonate (1.45 g, 3.8 mmol) in butyronitrile (5 ml) was stirred at 125° C. for 2 h. Then the mixture was cooled to r.t., the inorganic material was removed by filtration and washed with ethyl acetate. The combined organic solutions were concentrated in vacuo, and the product purified by flash chromatography on silica gel (ethyl acetate/methanol). Yield 200 mg (51%) of a brown oil.

후처리

  1. temperatureThen the mixture was cooled to r.t.
  2. customthe inorganic material was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe combined organic solutions were concentrated in vacuo
  5. customthe product purified by flash chromatography on silica gel (ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-e6928cab26d14140abfb4d19f912ec65
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143290B2

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