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

HRID 13158

反応式

HRID 13158 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8008Butyronitrile溶媒

反応条件

温度
125 °C

実験手順

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 acetete. 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.

後処理

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

出典と根拠

ORDレコード
ord-36e1dcf13e4e41959da051f6f8d727ca
出典データセット
uspto-grants-2010_06
特許番号
US07728030B2

関連ノート

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