Water → HCID 70046826、化合物

HRID 233643ノート

反応式

HRID 233643 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.S(O[CH2:22][CH2:23][O:24][C@H:25]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[C@H:27]([CH2:28][CH2:29][C@@H:30]3[C@@H:39]2[CH2:38][CH2:37][C@@:35]2([CH3:36])[C@:31]3([OH:49])[CH2:32][CH2:33][C@@H:34]2[C:44]2[CH:48]=[CH:47][O:46][CH:45]=2)[CH2:26]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[N:6]1([CH2:5][CH2:4][O:3][CH2:22][CH2:23][O:24][C@H:25]2[CH2:42][CH2:41][C@@:40]3([CH3:43])[C@H:27]([CH2:28][CH2:29][C@@H:30]4[C@@H:39]3[CH2:38][CH2:37][C@@:35]3([CH3:36])[C@:31]4([OH:49])[CH2:32][CH2:33][C@@H:34]3[C:44]3[CH:48]=[CH:47][O:46][CH:45]=3)[CH2:26]2)[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 86748784HCID 86748784、化合物

生成物 1

HCID 70046826HCID 70046826、化合物収率 86.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 0.13 g of NaH (60% dispersion in mineral oil) in 15 ml of anhydrous dimethylformamide, 0.37 g of 1-(2-hydroxyethyl)pyrrolidine were added at room temperature in a nitrogen atmosphere. The mixture was kept at reflux for 2 hrs, then 0.90 g of 3β-(2-tosyloxy-ethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, prepared as an intermediate in Ex. 7, were added. The mixture was kept at reflux temperature for 4 hrs; then 50 ml of water were added cautiously. The residue was extracted with methylene chloride, the organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using acetone/methanol 85/15 as eluant to give 0.70 g of the title compound (I-ah) as a light yellow solid.

後処理

  1. additionwere added at room temperature in a nitrogen atmosphere
  2. temperatureat reflux for 2 hrs
  3. addition7, were added
  4. temperatureat reflux temperature for 4 hrs
  5. extractionThe residue was extracted with methylene chloride
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe crude product was purified by flash-chromatography (SiO2)

出典と根拠

ORDレコード
ord-4621b55fb6bf4bc8a2356ed01ef0a08b
出典データセット
uspto-grants-1997_01
特許番号
US05593982

反応ノート

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