Ethylenediamine → HCID 86740722, compound

HRID 1380493Notes

Reaction equation

HRID 1380493 reaction equation
[CH3:1][O:2][C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:22])[CH:4]=1.[OH-].[K+].[CH2:25](N)[CH2:26]N.C#C>C(O)(C)(C)C.C1COCC1>[C:25]([C@@:12]1([OH:22])[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C@:18]1([CH3:21])[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH2:20][CH2:19]1)=[CH:6][CH2:7]3)#[CH:26]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 6326AcetyleneHCID 14797Potassium HydroxideHCID 926873-Methoxyandrosta-3,5-dien-17-one

Product 1

HCID 86740722HCID 86740722, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In an inert pressurizable vessel is placed 3-methoxyandrosta-3,5-dien-17-one (I Aa, 15 g) THF (60 ml), milled potassium hydroxide (15 g), t-butanol (1.5 ml), and ethylenediamine (10 ml). The stirred mixture is heated to 53° and a 15-pound partial pressure of acetylene is applied. These conditions are maintained for 3 hr at which time TLC indicates a mixture of ethisterone methyl enol ether and epiethisterone methyl enol ether. The reaction mixture is quenched with phosphate buffer (pH=7) and methylene chloride is used to isolate the product as an oil. The resulting oil is crystallized from toluene to give epi-ethisterone enol ether of approximately 90% purity.

Workup

  1. customIn an inert pressurizable vessel is placed
  2. temperatureThe stirred mixture is heated to 53°
  3. temperatureThese conditions are maintained for 3 hr at which time TLC
  4. customThe reaction mixture is quenched with phosphate buffer (pH=7) and methylene chloride

Sources & evidence

ORD record
ord-226da839add84c4a92880bb74e6f1958
Source dataset
uspto-grants-1986_04
Patent number
US04582644

Reaction notes

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