Morpholine → 21-Morpholino-5alpha-pregnane-3,11,20-trione

HRID 1576785Notes

Reaction equation

HRID 1576785 reaction equation
Cl[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O1CCCC1.O>[O:29]1[CH2:30][CH2:31][N:26]([CH2:2][C:3](=[O:25])[C@@H:4]2[C@:21]3([CH3:22])[C@H:7]([C@H:8]4[C@H:18]([C:19](=[O:23])[CH2:20]3)[C@:16]3([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]3)[CH2:10][CH2:9]4)[CH2:6][CH2:5]2)[CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 8673403321-Chloro-5alpha-pregnane-3,11,20-trione

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

21-Chloro-5α-pregnane-3,11,20-trione (200 mg.) in dry tetrahydrofuran (4 ml.) was treated with morpholine (0.20 ml.), and the solution was refluxed for 21/2 hours, and then left at room temperature for 3 days. The solution was diluted with water and extracted with chloroform. The organic solution was washed with water, dried over sodium sulphate and evaporated to a white foam (210 mg.), which was purified by preparative TLC in ethyl acetate to give 21-morpholino-5α-pregnane-3,11,20-trione (88 mg.) as a white foam, [α]D + 99°, (c 0.59). Treatment of this product in similar manner to that described in Example 50 gave title compound.

Workup

  1. temperaturethe solution was refluxed for 21/2 hours
  2. extractionextracted with chloroform
  3. washThe organic solution was washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to a white foam (210 mg.), which
  6. customwas purified by preparative TLC in ethyl acetate

Sources & evidence

ORD record
ord-52c5e9492ac743f59a44669445554acf
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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