Water → HCID 22789170, compound

HRID 1606359Notes

Reaction equation

HRID 1606359 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C@H:6]1[CH2:28][C@@:27]2([CH3:29])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:26]2[C:25](=[O:30])[CH2:24][C@@:23]2([CH3:31])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17]2(OCC[O:19]2)[CH3:18])[CH2:8][C@@H:7]1[OH:32].O.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>>[OH:32][C@@H:7]1[C@@H:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH2:28][C@@:27]2([CH3:29])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:26]2[C:25](=[O:30])[CH2:24][C@@:23]2([CH3:31])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1

Participants

4

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 22789161HCID 22789161, compound

Product 1

HCID 22789170HCID 22789170, compound

Procedure

2β-(3'-Chloropropoxy)-20,20-ethylenedioxy-3α-hydroxy-5α-pregnan-11-one (500 mg.) was dissolved in morpholine (5 ml.) and the solution heated on a steambath for 8 hours. The solution was poured into water and the precipitate extracted into ether (70 ml.). The ethereal solution was washed with water, dried over anhydrous sodium sulphate and evaporated to a white foam (480 mg.) which was dissolved in 35% aqueous acetic acid and the solution heated on a steam-bath for 3 hours. The solution was cooled in ice and an ice-cooled solution of 10N-potassium hydroxide added to the stirred solution in the presence of ether (100 ml.) until the aqueous layer was basic. The aqueous layer was extracted with ether (50 ml.) and the combined ether extracts washed with water, dried over anhydrous sodium sulphate and evaporated to a white foam (390 mg.) which was purified by preparative TLC in acetone to give the title compound (250 mg.) as a white foam, [α](c D + 65.0° (C 1.02).

Workup

  1. temperaturethe solution heated on a steambath for 8 hours
  2. extractionthe precipitate extracted into ether (70 ml.)
  3. washThe ethereal solution was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to a white foam (480 mg.) which
  6. dissolutionwas dissolved in 35% aqueous acetic acid
  7. temperaturethe solution heated on a steam-bath for 3 hours
  8. temperatureThe solution was cooled in ice
  9. temperaturean ice-cooled solution of 10N-potassium hydroxide
  10. additionadded to the stirred solution in the presence of ether (100 ml.) until the aqueous layer
  11. extractionThe aqueous layer was extracted with ether (50 ml.)
  12. washthe combined ether extracts washed with water
  13. dry with materialdried over anhydrous sodium sulphate
  14. customevaporated to a white foam (390 mg.) which
  15. customwas purified by preparative TLC in acetone

Sources & evidence

ORD record
ord-501e59a5bc5f4301bf5e7fdf4e251d13
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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