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

HRID 233655노트

반응식

HRID 233655 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9cb8bfa664f747318c002326dc145f52
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593982

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