Morpholine → HCID 54054826, compound

HRID 1576781Notes

Reaction equation

HRID 1576781 reaction equation
Br[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:11](=[CH:12][C@H:13]([OH: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>[OH:24][C@@H:13]1[CH:14]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:15][C@@:16]2([CH3:17])[C:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[C:19](=[O:23])[CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:25])[CH3:2])=[CH:12]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86734029HCID 86734029, compound

Product 1

HCID 54054826HCID 54054826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21-Bromo-3α-hydroxypregn-4-ene-11,20-dione (150 mg.) in tetrahydrofuran (5 ml.) was treated with morpholine (0.1 ml.) and the stirred mixture was refluxed under nitrogen for 2 hours, during which time a white precipitate formed. The mixture was partitioned between methylene chloride and water. The aqueous layer was extracted with more methylene chloride and the combined organic extracts were washed with water, dried over sodium sulphate and evaporated to a foam (152 mg.) which was purified by preparative T.L.C. in acetone/petrol 1/1, the main band Rf 0.3-0.45 being separated to give title compound (99 mg.) as a white foam, [α]D + 174° (c 0.12)

Workup

  1. temperaturethe stirred mixture was refluxed under nitrogen for 2 hours, during which time a white precipitate
  2. customformed
  3. customThe mixture was partitioned between methylene chloride and water
  4. extractionThe aqueous layer was extracted with more methylene chloride
  5. washthe combined organic extracts were washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated to a foam (152 mg.) which
  8. customwas purified by preparative T.L.C
  9. customin acetone/petrol 1/1, the main band Rf 0.3-0.45 being separated

Sources & evidence

ORD record
ord-6ede4978d8e94f948b544856d9cf2b12
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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