HCID 86735422, compound → HCID 86735423, compound

HRID 1834958Notes

Reaction equation

HRID 1834958 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH2:28][OH:29])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:30])[CH2:11]1>CO.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[OH:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH2:28][OH:29])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:30])[CH2:11]1

Participants

4

Reactant 1

HCID 86735422HCID 86735422, compound

Product 1

HCID 86735423HCID 86735423, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3β,19-dihydroxyandrost-5-en-17-one diacetate in methanol is hydrogenated with a 10% Palladium-on-charcoal catalyst at atmospheric pressure for 8 hours. The catalyst is removed by filtration and the filtrate concentrated to a small volume, cooled, and filtered to yield the desired 3β,19-dihydroxy-5α-androstan-17-one diacetate. Recrystallization from hexane results in pure material.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated to a small volume
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4502aa0643554a1589bab94ffd8c6766
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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