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

HRID 1576794Notes

Reaction equation

HRID 1576794 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@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.O>O1CCCC1>[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 3

HCID 962WaterHCID 8083MorpholineHCID 8673347421-Bromo-5alpha-pregnane-3,11,20-trione

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21-bromo-5α-pregnane-3,11,20-trione (500 mg) in dry tetrahydrofuran was treated at reflux with morpholine (0.5 ml) for 1/2 hour, and poured into water. The oily precipitate was extracted into ether and the extracts were washed with water, dried (Na2SO4) and evaporated to the crude product which was purified by preparative t.l.c. in ethyl acetate and crystallisation from ether to give the title compound (220 mg). m.p. 159°-164°C [α]D +98° (c=1.1%)

Workup

  1. extractionThe oily precipitate was extracted into ether
  2. washthe extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated to the crude product which
  5. customwas purified by preparative t.l.c
  6. customin ethyl acetate and crystallisation from ether

Sources & evidence

ORD record
ord-c0680a7ade3741f5a799f8210d04c6d7
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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