Hydrochloric Acid → HCID 11674487, compound

HRID 1488940Notes

Reaction equation

HRID 1488940 reaction equation
CC([Si](C)(C)[O:6][CH:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C:16]2([C:27]2[CH:31]=[CH:30][O:29][CH:28]=2)O)[CH2:8]1)(C)C.Cl.C(Cl)Cl>O1CCOCC1>[O:29]1[CH:30]=[CH:31][C:27]([C:16]2[C@:17]3([CH2:19][CH2:20][C@H:21]4[C@@H:12]([CH2:11][CH:10]=[C:9]5[C@:22]4([CH3:25])[CH2:23][CH2:24][C@H:7]([OH:6])[CH2:8]5)[C@@H:13]3[CH2:14][CH:15]=2)[CH3:18])=[CH:28]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 131720224HCID 131720224, compound

Product 1

HCID 11674487HCID 11674487, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine (3β,17β)-3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(3-furanyl)-androst-5-en-17-ol (2.50 g, 5.31 mmol) prepared as in Scheme III, step B above, with 4N hydrogen chloride in 1,4-dioxane (35 mL) under an atmosphere of nitrogen. Stir the reaction for 40 minutes at room temperature and then dilute the reaction with methylene chloride (150 mL). Wash the organic layer with water (35 mL), saturated sodium bicarbonate (2×50 mL), brine (30 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (ethyl acetate/hexane, 3:7, silica gel) to provide 1.05 g of product as a white solid. Recrystallize a portion of the product from aqueous acetone and dry under high vacuum over refluxing ethanol for 4 hours to provide the title compound as a white crystallize solid, Rf =0.43 (ethyl acetate/hexane, 35:65, silica gel), mp 186°-189° C.; 1H NMR (CDCl3) δ7.47 (broad singlet, 1H), 7.36 (t, 1H, J=1.7 Hz), 6.48 (dd, 1H, J=0.8, 1.8 Hz), 5.83 (dd, 1H, J=1.9, 3.2 Hz), 5.41-5.37 (m, 1H), 3.60-3.48 (m, 1H), 1.07 (s, 3H), 0.96 (s, 3H); MS (CI/CH4) m/z (rel. intensity) 339 (MH+, 68), 338 (55), 337 (28), 321 (100); HRMS C23H31O2 (MH+) calcd 339.2324, observed 339.2304.

Workup

  1. customthe reaction for 40 minutes at room temperature
  2. additiondilute
  3. washWash the organic layer with water (35 mL), saturated sodium bicarbonate (2×50 mL), brine (30 mL)
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customPurify the residue by flash chromatography (ethyl acetate/hexane, 3:7, silica gel)

Sources & evidence

ORD record
ord-ccab5efce43f428c93d0f689c313622b
Source dataset
uspto-grants-1997_10
Patent number
US05677293

Reaction notes

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