Benzyl Bromide → 17beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5alpha-androstan-3-one

HRID 1744793ノート

反応式

HRID 1744793 の反応式
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[C:36]([OH:38])[CH:35]=[C:34]([OH:39])[CH:33]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[C:34]([OH:39])[CH:35]=[C:36]([O:38][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:37]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6962692817beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3,5-dihydroxyphenyl)propyl)-5alpha-androstan-3-one

生成物 1

HCID 6962670717beta-(Tert-butyldimethylsilyloxy)-7alpha-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5alpha-androstan-3-one収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

17β-(tert-Butyldimethylsilyloxy)-7α-(3-(3,5-dihydroxyphenyl)propyl)-5α-androstan-3-one (75 mg), benzyl bromide (16.9 μl) and potassium carbonate (56 mg) were suspended in DMF (1 ml) and stirred overnight at 25° C. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate and then washed with water and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and then filtered. After evaporation under reduced pressure to remove the solvent, the resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/4) to give 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3-benzyloxy-5-hydroxyphenyl)propyl)-5α-androstan-3-one (21.0 mg, yield 24%).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water and saturated aqueous sodium chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customAfter evaporation under reduced pressure
  6. customto remove the solvent

出典と根拠

ORDレコード
ord-cdc2725241144bcaa3f001ef714a0d62
出典データセット
uspto-grants-2006_03
特許番号
US07018993B2

反応ノート

読み込み中…