Sodium Chloride → 14beta-Methoxy-17beta-(3-furyl)-5beta-androstan-3beta-ol

HRID 1647644ノート

反応式

HRID 1647644 の反応式
[Si]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@:15]3([O:33][CH3:34])[CH2:16][CH2:17][C@@H:18]2[C:28]2[CH:32]=[CH:31][O:30][CH:29]=2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>>[CH3:34][O:33][C@@:15]12[C@H:14]3[C@@H:23]([C@:24]4([CH3:27])[C@H:11]([CH2:12][CH2:13]3)[CH2:10][C@@H:9]([OH:8])[CH2:26][CH2:25]4)[CH2:22][CH2:21][C@:19]1([CH3:20])[C@@H:18]([C:28]1[CH:32]=[CH:31][O:30][CH:29]=1)[CH2:17][CH2:16]2

参加物

4

反応物 3

HCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 700444293beta-Tert-butyldimethylsilyloxy-14beta-methoxy-17beta-(3-furyl)-5beta-androstane

生成物 1

HCID 7004361914beta-Methoxy-17beta-(3-furyl)-5beta-androstan-3beta-ol収率 87.1%

実験手順

A solution of 3.0 g of 3β-tert-butyldimethylsilyloxy-14β-methoxy-17β-(3-furyl)-5β-androstane in 57 ml of a 1.0 M solution of tetrabutylammonium fluoride was heated at 70° C. under nitrogen for an hr and then poured into a saturated solution of sodium chloride. The mixture was extracted with ethyl acetate and the organic layer was dried over sodium sulfate, evaporated to dryness under reduced pressure and purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 2.0 g of the title compound (II-c) as a white solid.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure
  4. custompurified by flash-chromatography (SiO2)

出典と根拠

ORDレコード
ord-a56f64cb6aa143598388ea802e61bc4e
出典データセット
uspto-grants-1995_07
特許番号
US05432169

反応ノート

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