Acetone → HCID 10339275, compound

HRID 1077586Notes

Reaction equation

HRID 1077586 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:7]12[CH3:8])[C@:20]1([CH3:21])[C:15]([CH2:16][C@@H:17]([O:25][Si](C(C)C)(C(C)C)C(C)C)[CH2:18][CH2:19]1)=[N:14][CH2:13]3)=[O:5])[CH3:2].CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>C(#N)C.C(Cl)Cl>[CH2:36]([N:3]([CH2:1][CH3:2])[C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:7]12[CH3:8])[C@:20]1([CH3:21])[C:15](=[CH:16][C:17](=[O:25])[CH2:18][CH2:19]1)[NH:14][CH2:13]3)=[O:5])[CH3:37]

Participants

7

Reactant 4

HCID 180AcetoneHCID 3776IsopropanolHCID 15343381HCID 15343381, compoundHCID 131709961Jones' reagent

Product 1

HCID 10339275HCID 10339275, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 17β-N,N-diethylcarbamoyl-3β-triisopropylsilyloxy-6-azaandrost-5-ene (1.51 g, 2.8 mmol) in acetonitrile (100 mL) at 0° C. is treated with 48% aqueous HF (20 mL), the reaction allowed to warm to room temperature and stirred for 2 hours. The solution is then diluted with methylene chloride (200 mL), washed with H2O and saturated aqueous bicarbonate, dried over MgSO4 and concentrated to an off-white solid; yield 1.02 g crude (96%). A solution of this solid (0.48 g, 1.3 mmol) in acetone (100 mmol) is treated with Jones reagent (1 mL, 3.22M, 3.2 mmol) and warmed to room temperature. Next, isopropanol is added (10 mL), the reaction concentrated, the residue dissolved in ethyl acetate (75 mL), washed with saturated aqueous bicarbonate, dried over MgSO4 and concentrated to give 17β-N,N-diethylcarbamoyl-6-azaandrost-4-en-3-one as an off-white solid; yield: 0.22 g (46%). This material is then triturated with ether to give 172 mg pure white solid; m.p. 253°-256° C. (dec.). Anal. Calcd. for C23H36N2O2 ; C, 74.15; H, 9.74; N, 7.52. Found: C, 73.88; H, 9.77; N, 7.44.

Workup

  1. washwashed with H2O and saturated aqueous bicarbonate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to an off-white solid
  4. temperaturewarmed to room temperature
  5. concentrationthe reaction concentrated
  6. dissolutionthe residue dissolved in ethyl acetate (75 mL)
  7. washwashed with saturated aqueous bicarbonate
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ed2742a7c8c746158b07dc7eeeca0a54
Source dataset
uspto-grants-1996_08
Patent number
US05543406

Reaction notes

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