21-Morpholino-5alpha-pregnane-3,11,20-trione → 3alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione

HRID 1576784Notes

Reaction equation

HRID 1576784 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8](=[O:30])[C@@H:9]2[C@:26]3([CH3:27])[C@H:12]([C@H:13]4[C@H:23]([C:24](=[O:28])[CH2:25]3)[C@:21]3([CH3:22])[C@H:16]([CH2:17][C:18](=[O:29])[CH2:19][CH2:20]3)[CH2:15][CH2:14]4)[CH2:11][CH2:10]2)[CH2:3][CH2:2]1>O>[OH:29][C@@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[C:24](=[O:28])[CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C:8](=[O:30])[CH2:7][N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:17]1

Participants

3

Reactant 1

HCID 8673403221-Morpholino-5alpha-pregnane-3,11,20-trione

Product 1

HCID 867340213alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 21-morpholino-5α-pregnane-3,11,20-trione (100 mg.) in the "stock" hloroiridic solution (see preparation 6 below) (10 ml.), was refluxed for 14 hours. The cooled mixture was poured into water and made just alkaline. The slight oily precipitate was extracted into ethyl acetate and the extracts were washed with water, dried (Na2SO4), and evaporated to give essentially the title compound, shown by n.m.r. spectroscopy and T.L.C. (Rf 0.16) on silica in ethyl acetate to be identical to the product of Example 38.

Workup

  1. temperaturewas refluxed for 14 hours
  2. extractionThe slight oily precipitate was extracted into ethyl acetate
  3. washthe extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-6af6eaab32cb46feb5e8f3970243b299
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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