Water → HCID 86738082, compound

HRID 848777Notes

Reaction equation

HRID 848777 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=O)[C@H:15]([CH3:22])[CH2:16]1)[CH2:11][CH2:10]3.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[N:25][OH:26])[C@H:15]([CH3:22])[CH2:16]1)[CH2:11][CH2:10]3

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 70562008HCID 70562008, compound

Product 1

HCID 86738082HCID 86738082, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 17β-methoxy-2α-methyl-5α-androstan-3-one (Acta. Endocrinology 36, 83 (1961), 0.5 g.), hydroxylamine hydrochloride (0.218 g.) and sodium acetate (0.258 g.) in ethanol (20 ml.) is refluxed for 1 hour. Water is then added; a precipitate forms which is filtered, washed, dried and recrystallized from methylene chloride-acetone to give the title compound, m.p. 203°-211°; IR (mull) 3360 and 1650 cm-1 ; MS (me) 333; NMR (CDCl3) 0.75, 0.93, 1.06, 3.15 and 3.33 δ.

Workup

  1. temperatureis refluxed for 1 hour
  2. filtrationa precipitate forms which is filtered
  3. washwashed
  4. customdried
  5. customrecrystallized from methylene chloride-acetone

Sources & evidence

ORD record
ord-09f2569b1fbb464c8eefaddcb1adb649
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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