Water → 7-[O-(3-chloropropyl)oximino]-5-androstene-3beta,17beta-diol diacetate

HRID 1808756Notes

Reaction equation

HRID 1808756 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[N:28][OH:29])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][CH2:39][Cl:40].O>CC(CC)=O>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[N:28][O:29][CH2:37][CH2:38][CH2:39][Cl:40])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 867617537-Oximino-5-androstene-3beta,17beta-diol Diacetate

Product 1

HCID 867617547-[O-(3-chloropropyl)oximino]-5-androstene-3beta,17beta-diol diacetateYield 58.82%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 7-oximino-5-androstene-3β,17β-diol diacetate (1 g, 2.48 mmol) and anhydrous potassium carbonate (2 g) was stirred and refluxed in ethyl methyl ketone (100 Ml) at 110° C. for 3 h. 1-Bromo-3-chloropropane (0.25 Ml, 2.48 mmol) was added to the reaction mixture and further refluxed for 20 h with continuous stirring. The completion of the reaction was monitored by TLC. The slurry was cooled, filtered and excess of solvent was removed under reduced pressure to obtain an oily residue. Iced water was added to the oily residue and it was allowed to stand overnight. The precipitate obtained was filtered, washed with water, dried and crystallized from pet-ether (60-80° C.) to afford 7-[O-(3-chloropropyl)oximino]-5-androstene-3β,17β-diol diacetate (23) (0.7 g, 58.82%), mp 155° C. (Decomp).

Workup

  1. temperaturefurther refluxed for 20 h with continuous stirring
  2. temperatureThe slurry was cooled
  3. filtrationfiltered and excess of solvent
  4. customwas removed under reduced pressure
  5. customto obtain an oily residue
  6. customThe precipitate obtained
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried
  10. customcrystallized from pet-ether (60-80° C.)

Sources & evidence

ORD record
ord-381c127beb7f45868c2e11246512e97c
Source dataset
uspto-grants-2013_01
Patent number
US08361996B2

Reaction notes

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