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

HRID 1733092Notes

Reaction equation

HRID 1733092 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

To a solution of 1α-methyl-4-androstene-17β,19-diol dipropionate in 10% aqueous methanol is added 1 equivalent sodium bicarbonate and the solution is heated under reflux for one hour. Methanol is removed under vacuum to half volume and the concentrate is poured onto water. The solid is filtered, air dried and crystallized from hexane to give 1α-methyl-4-androstene-17β,19-diol 17-propionate.

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for one hour
  3. customMethanol is removed under vacuum to half volume
  4. additionthe concentrate is poured onto water
  5. filtrationThe solid is filtered
  6. customair dried
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-469939cb380142c0b0011e13d7ed5b35
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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