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Trifluoroacetic acid → (11beta,17beta)-17-(Ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one

HRID 371060
Notes
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Reaction equation

HRID 371060 reaction equation
[CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl.C(Cl)(Cl)Cl.CCCCCC>[CH2:1]([S:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 1291771217-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

Product 1

HCID 70401069(11beta,17beta)-17-(Ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-oneYield 85.9%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 21585165Chloroform hexaneSolvent

Procedure

To a homogeneous solution of 600 mg (1.66 mmole) of 17-(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4,16-trien-3-one in a mixture of dry dichloromethane (60 ml) and trifluoroacetic acid (207 mg) was added triethylsilane (230 mg) and the mixture was stirred at room temperature under a nitrogen atmosphere for 2.5 hours. Since the tlc of an aliquot showed incomplete reaction, more trifluoroacetic acid (207 mg) and triethylsilane (230 mg) were added. After 1.5 hours the starting material had disappeared by tlc. The resulting solution was diluted with dichloromethane, washed with saturated sodium bicarbonate solution and water, dried (anhydrous sodium sulfate) and evaporated in vacuo to give a solid. This was redissolved in 1:4 hexane chloroform and chromatographed on a 30 g silica gel column. Elution with 1:4 hexane-chloroform, chloroform and 5:95 ethyl acetate-chloroform gave 520 mg of a tlc-homogeneous title compound. Crystallization from acetone-hexane gave 410 mg of an analytical specimen, melting point 223°-225° C., with consistent spectral data.

Workup

  1. additionwere added
  2. waitAfter 1.5 hours the starting material had disappeared by tlc
  3. washwashed with saturated sodium bicarbonate solution and water
  4. dry with materialdried (anhydrous sodium sulfate)
  5. customevaporated in vacuo
  6. customto give a solid
  7. customchromatographed on a 30 g silica gel column
  8. washElution with 1:4 hexane-chloroform, chloroform and 5:95 ethyl acetate-chloroform

Sources & evidence

ORD record
ord-47aa9269b1f14dc58a4ad14220c8a794
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04529548

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes