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

HRID 1647644Notes

Reaction equation

[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

Participants

Reactant 3

HCID 5234Sodium Chloride

HCID 2724141Tetrabutylammonium Fluoride

HCID 700444293beta-Tert-butyldimethylsilyloxy-14beta-methoxy-17beta-(3-furyl)-5beta-androstane

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a56f64cb6aa143598388ea802e61bc4e
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05432169

Reaction notes

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