1,1-Dimethylhydrazine → (3S,5R,8R,9S,10S,13R,14S,17S)-17-[(E)-(dimethylhydrazinylidene)methyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diol

HRID 1735738ノート

反応式

HRID 1735738 の反応式
[CH3:1][N:2]([CH3:4])[NH2:3].[OH:5][C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@:12]3([OH:27])[CH2:13][CH2:14][C@@H:15]2[CH:25]=O)[CH2:7]1.C([O-])(O)=O.[Na+]>O.O1CCOCC1>[CH3:1][N:2]([CH3:4])/[N:3]=[CH:25]/[C@H:15]1[CH2:14][CH2:13][C@:12]2([OH:27])[C@H:11]3[C@H:20]([CH2:19][CH2:18][C@:16]12[CH3:17])[C@:21]1([CH3:24])[C@@H:8]([CH2:7][C@@H:6]([OH:5])[CH2:23][CH2:22]1)[CH2:9][CH2:10]3

参加物

6

反応物 3

HCID 59761,1-DimethylhydrazineHCID 516892Sodium BicarbonateHCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde

生成物 1

HCID 88124783(3S,5R,8R,9S,10S,13R,14S,17S)-17-[(E)-(dimethylhydrazinylidene)methyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 0.80 g of NaH2PO4.H2O, 1.70 g of Na2HPO4.12H2O and 0.12 ml of N,N-dimethylhydrazine in 200 ml of water a solution of 0.64 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 20 ml of dioxane was added dropwise at room temperature. After 1.5 hrs the solution was alkalinized with an acqueous solution of NaHCO3 and extracted with ethyl acetate; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash-chromatography (SiO2) using cyclohexane/chloroform/acetone 4/3/3 as eluant to give 0.37 g of the title compound (I-ai), as a white foam.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash-chromatography (SiO2)

出典と根拠

ORDレコード
ord-3c381e1a763a4967ab4a7b99e58839aa
出典データセット
uspto-grants-1996_07
特許番号
US05538960

反応ノート

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