Morpholine → HCID 22789169, compound

HRID 1606357Notes

Reaction equation

HRID 1606357 reaction equation
Cl[CH2:2][CH2:3][O:4][C@H:5]1[CH2:27][C@@:26]2([CH3:28])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:25]2[C:24](=[O:29])[CH2:23][C@@:22]2([CH3:30])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16]2(OCC[O:18]2)[CH3:17])[CH2:7][C@@H:6]1[OH:31].[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[OH:31][C@@H:6]1[C@@H:5]([O:4][CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH2:27][C@@:26]2([CH3:28])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:25]2[C:24](=[O:29])[CH2:23][C@@:22]2([CH3:30])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C:16](=[O:18])[CH3:17])[CH2:7]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 22789157HCID 22789157, compound

Product 1

HCID 22789169HCID 22789169, compound

Procedure

2β-(2'-Chloroethoxy)-20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one (500 mg.) was dissolved in morpholine (15 ml.) and the solution heated on a steam-bath for 24 hours. The morpholine was removed by evaporating in vacuo and the resulting red oil was dissolved in 35% aqueous acetic acid (25 ml.). This solution was heated on a steam-bath for 21/2 hours. Water (50 ml.) was added and the slightly turbid solution filtered through Kieselguhr. The filtrate was made alkaline with 10N-potassium hydroxide and the precipitate extracted into ether (100 ml.). The ether extract was washed with water until the aqueous layer was neutral, dried over anhydrous sodium sulphate and evaporated to give the title compound as a white foam (250 mg.) [α]D + 82° (c 0.98).

Workup

  1. temperaturethe solution heated on a steam-bath for 24 hours
  2. customThe morpholine was removed
  3. customby evaporating in vacuo
  4. dissolutionthe resulting red oil was dissolved in 35% aqueous acetic acid (25 ml.)
  5. temperatureThis solution was heated on a steam-bath for 21/2 hours
  6. additionWater (50 ml.) was added
  7. filtrationthe slightly turbid solution filtered through Kieselguhr
  8. extractionthe precipitate extracted into ether (100 ml.)
  9. extractionThe ether extract
  10. washwas washed with water until the aqueous layer
  11. dry with materialdried over anhydrous sodium sulphate
  12. customevaporated

Sources & evidence

ORD record
ord-c5b7a3307d974a77910670864c129c43
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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