Hydrochloric Acid → 17-(3-Pyridinyl)androsta-4,16-dien-3-one

HRID 1451364

Reaction equation

HRID 1451364 reaction equation
FC1C(F)=C(C(F)(F)F)C(F)=C(F)C=1[O:4][C:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:6]=1.C(O)C.Cl.[OH-].[Na+]>C1COCC1.O>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([C:14]2[C@:15]3([CH2:17][CH2:18][C@H:19]4[C@@H:10]([CH2:9][CH2:8][C:7]5[C@:20]4([CH3:23])[CH2:21][CH2:22][C:5](=[O:4])[CH:6]=5)[C@@H:11]3[CH2:12][CH:13]=2)[CH3:16])[CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 541885633-[2,3,5,6-Tetrafluoro-4-(trifluoromethyl)phenoxy]-17-(3-pyridinyl)androsta-3,5,16-triene

Product 1

HCID 19694117-(3-Pyridinyl)androsta-4,16-dien-3-oneYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To solution of 3-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy]-17-(3-pyridyl)androsta-3,5,16-triene (0.423 g, 0.75 mmol) in THF (5 ml) was added ethanol (5 ml) followed by aqueous hydrochloric acid (1M, 5 ml) and the mixture heated, with stirring, by an oil bath at 65° C. for 48h and allowed to cool. The mixture was poured into water (20 ml), neutralised with aqueous sodium hydroxide (1M), and extracted with diethyl ether (3×30 ml). The ether extracts were combined, dried (Na2CO3), and concentrated. Chromatography, on elution with diethyl ether, afforded the title compound (185 mg, 71%) which crystallised from diethyl ether, m.p. 148°-150° C. IR νmax 1674 cm- ; 1H-NMR(CDCl3) inter alia δ1.07(3H,s,18-CH3), 1.24(3H,s,19-CH3), 5.76(1H,s,4-H), 5.99(1H,m,16-H), 7.23(1H,m,Py 5-H), 7.64(1H,m,Py 4-H), 8.47(1H,m,Py 6-H), 8.62(1H,m,Py 2-H); MS m/z 347 (M+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto cool
  3. extractionextracted with diethyl ether (3×30 ml)
  4. dry with materialdried (Na2CO3)
  5. concentrationconcentrated
  6. washChromatography, on elution with diethyl ether

Sources & evidence

ORD record
ord-4796ff01b42f4112a7e3d0c9adcf17ca
Source dataset
uspto-grants-1997_02
Patent number
US05604213

Linked notes

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