Sodium hydride → (1aS,5aR,7aS,8S,10cS)-5a,7a-dimethyl-3-oxo-N-phenyl-1,1a, 3,4,5,5a,5b,6,7,7a,8,9,10,10a,10b,10c-hexadecahydro-cyclopenta[a]cyclopropa[1]phenanthrene-8-carboxamide

HRID 749055ノート

反応式

HRID 749055 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[O:9]=[C:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12]([CH:13]=[CH:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2C(F)(F)F)=[O:30])=[CH:11]1>CS(C)=O>[CH3:28][C@:25]12[CH2:26][CH2:27][C:10](=[O:9])[CH:11]=[C:12]1[C@H:13]1[CH2:4][C@H:14]1[CH:15]1[CH:24]2[CH2:23][CH2:22][C@:20]2([CH3:21])[C@@H:19]([C:29]([NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:30])[CH2:18][CH2:17][CH:16]21

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 68976085(17beta)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamide

生成物 1

HCID 86594839(1aS,5aR,7aS,8S,10cS)-5a,7a-dimethyl-3-oxo-N-phenyl-1,1a, 3,4,5,5a,5b,6,7,7a,8,9,10,10a,10b,10c-hexadecahydro-cyclopenta[a]cyclopropa[1]phenanthrene-8-carboxamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a suspension of NaH (0.25 g, 6.18 mmol) in 7.4 mL DMSO (dried over molecular sieves) at room temperature under N2 was added trimethylsulfoxonium iodide (1.50 g, 6.85 mmol). The mixture was stirred for 1.5 hr. A solution of (17β)-3-oxo-N-[2-(trifluoromethyl)phenyl]androsta-4,6-diene-17-carboxamide (5-1) (0.68 g, 1.49 mmol) in 10 mL DMSO was added slowly. The solution was stirred at room temperature overnight. The reaction was then quenched by dropwise addition of 10% KHSO4 solution and extracted with CHCl3. The organic phase was washed with 10% KHSO4 solution, saturated NaHCO3 solution, and brine, then dried with MgSO4. After removal of the solvent, the residue was purified by chiral preparative HPLC (Chiralpak AD, 85% Hexanes (0.1% diethylamine); 15% 2-propanol) to yield the desired resolved products 6-6and 6-2.

後処理

  1. stirringThe solution was stirred at room temperature overnight
  2. customThe reaction was then quenched by dropwise addition of 10% KHSO4 solution
  3. extractionextracted with CHCl3
  4. washThe organic phase was washed with 10% KHSO4 solution, saturated NaHCO3 solution, and brine
  5. dry with materialdried with MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by chiral preparative HPLC (Chiralpak AD, 85% Hexanes (0.1% diethylamine); 15% 2-propanol)
  8. customto yield the

出典と根拠

ORDレコード
ord-b1c40ff6d2a2459c9507307259a3d36a
出典データセット
uspto-grants-2008_07
特許番号
US07402577B2

反応ノート

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