Sodium Bicarbonate → 1alpha-Methyl-4-androstene-17beta,19-diol 17-propionate

HRID 2397973Notes

Reaction equation

HRID 2397973 reaction equation
[C:1]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15](=[CH:16][CH2:17][CH2:18][C@@H:19]1[CH3:30])[CH2:14][CH2:13]3)(=[O:4])[CH2:2][CH3:3].C(=O)(O)[O-].[Na+]>CO>[C:1]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][OH:22])[C:15](=[CH:16][CH2:17][CH2:18][C@@H:19]1[CH3:30])[CH2:14][CH2:13]3)(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 705838891alpha-Methyl-4-androstene-17beta,19-diol dipropionate

Product 1

HCID 705847651alpha-Methyl-4-androstene-17beta,19-diol 17-propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1α-Methyl-4-androstene-17β,19-diol dipropionate is dissolved in a 10% aqueous methanol solution and one equivalent of sodium bicarbonate is added. The solution is stirred and heated at its reflux temperature for one hour and poured onto ice water with vigorous stirring. The precipitate is removed by filtration, air dried and crystallized from hexane to yield 1α-methyl-4-androstene-17β,19-diol 17-propionate.

Workup

  1. additionis added
  2. temperatureheated at its
  3. temperaturereflux temperature for one hour
  4. additionpoured onto ice water with vigorous stirring
  5. customThe precipitate is removed by filtration, air
  6. customdried
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-058026ca909142dd97a15bf7314057cc
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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