2beta-Ethyl-17beta-methoxy-5alpha-androstan-3-one → 2alpha-Ethyl-17beta-methoxy-5alpha-androstan-3-one

HRID 848775Notes

Reaction equation

HRID 848775 reaction equation
[CH2:1]([C@H:3]1[CH2:20][C@@:19]2([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[O:22][CH3:23])[CH2:5][C:4]1=[O:24])[CH3:2]>C(O)C.[OH-].[Na+]>[CH2:1]([C@@H:3]1[CH2:20][C@@:19]2([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[O:22][CH3:23])[CH2:5][C:4]1=[O:24])[CH3:2]

Participants

4

Reactant 1

HCID 705628222beta-Ethyl-17beta-methoxy-5alpha-androstan-3-one

Product 1

HCID 128368492alpha-Ethyl-17beta-methoxy-5alpha-androstan-3-one

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent

Procedure

2β-Ethyl-17β-methoxy-5α-androstan-3-one (Step A) is dissolved in ethanol (95%, 13 ml.) followed by addition of sodium hydroxide (50%, 14 drops). After stirring at 20°-25° for 4.5 hrs. the mixture is extracted with diethyl ether, the diethyl ether extract is concentrated under reduced pressure to yield the title compound, which is recrystallized twice from methanol; m.p. 105°-107°; NMR (CDCl3) 0.77, 1.05, 3.20 and 3.33 δ.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. extractionthe diethyl ether extract
  3. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-3363d3422175400f96ff40f04c7fae26
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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