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

HRID 233655ノート

反応式

HRID 233655 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 1.0M 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-9cb8bfa664f747318c002326dc145f52
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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