Water → Ethyl 11-[3,17beta-dihydroxyestra-1,3,5(10)-trien-7alpha-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoate

HRID 460470ノート

反応式

HRID 460470 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C:16]1[CH:15]=[CH:14][C:13]([O:20]C)=[CH:12][C:11]=1[CH2:10][C@H:9]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([CH2:37][CH2:38][CH2:39][C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])[C:32]([O:34][CH2:35][CH3:36])=[O:33].[Br-].[Br-].[Br-].B.O>ClCCl>[OH:20][C:13]1[CH:14]=[CH:15][C:16]2[C@@H:17]3[C@H:8]([C@H:5]4[C@@:3]([CH2:19][CH2:18]3)([CH3:4])[C@@H:2]([OH:1])[CH2:7][CH2:6]4)[C@H:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([CH2:37][CH2:38][CH2:39][C:40]([F:45])([F:46])[C:41]([F:42])([F:43])[F:44])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:10][C:11]=2[CH:12]=1

参加物

5

反応物 3

HCID 962WaterHCID 86588528Ethyl 11-[17beta-hydroxy-3-methoxyestra-1,3,5(10)-trien-7alpha-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoateHCID 178419136HCID 178419136、化合物

生成物 1

HCID 86588529Ethyl 11-[3,17beta-dihydroxyestra-1,3,5(10)-trien-7alpha-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoate収率 72%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Ethyl 11-[17β-hydroxy-3-methoxyestra-1,3,5(10)-trien-7α-yl]-2-(4,4,5,5,5-pentafluoropentyl)undecanoate (946 mg, 1.43 mmol) was dissolved in dichloromethane (18 ml). To this solution, a 1M solution of borane tribromide in dichloromethane (4.3 ml, 4.3 mmol) was added dropwise at −78° C. The reaction mixture was warmed slowly and stirred for 3 hours at 0° C. Water was added to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then filtered. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give ethyl 11-[3,17β-dihydroxyestra-1,3,5(10)-trien-7α-yl]-2-(4,4,5,5,5-pentafluoro-pentyl)undecanoate (663 mg, Yield 72%).

後処理

  1. temperatureThe reaction mixture was warmed slowly
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationAfter concentration under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-8dea40a69d024b63be1184a22de0ad64
出典データセット
uspto-grants-2007_03
特許番号
US07196081B2

反応ノート

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