Hydrochloric Acid → 3alpha-Hydroxy-21-morpholinomethyl-5alpha-pregnane-11,20-dione

HRID 1973719Notes

Reaction equation

HRID 1973719 reaction equation
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.Cl.[CH2:32]=O>C(O)(=O)C>[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH2:13][CH2:32][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 104845Alphaxalone

Product 1

HCID 227951753alpha-Hydroxy-21-morpholinomethyl-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3α-Hydroxy-5α-pregnane-11,20-dione (1.0 g) in glacial acetic acid (20 ml.) was treated with morpholine (1.0 ml) and concentrated hydrochloric acid (1.0 ml). Paraformaldehyde (600 mg) was added to the stirred solution which was then heated in an oil-bath at 95°-100° for 1 hour. The solution was evaporated and dried in vacuo to a yellow oil (3.5 g.) which was partitioned between ethyl acetate and 0.1N hydrochloric acid. The colourless organic layer was extracted with more hydrochloric acid and the combined yellow aqueous layer was washed with ethyl acetate and basified with saturated sodium bicarbonate solution. The cloudy precipitate was extracted into ethyl acetate, and the extract washed with water, dried (Na2SO4) and evaporated to a pale yellow foam (1.05 g) which was purified by preparative t.l.c. in acetone to give title compound (534 mg) as a colourless foam, [α]D + 73° (c, 0.81).

Workup

  1. temperaturewas then heated in an oil-bath at 95°-100° for 1 hour
  2. customThe solution was evaporated
  3. customdried in vacuo to a yellow oil (3.5 g.) which
  4. customwas partitioned between ethyl acetate and 0.1N hydrochloric acid
  5. extractionThe colourless organic layer was extracted with more hydrochloric acid
  6. washthe combined yellow aqueous layer was washed with ethyl acetate and basified with saturated sodium bicarbonate solution
  7. extractionThe cloudy precipitate was extracted into ethyl acetate
  8. washthe extract washed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated to a pale yellow foam (1.05 g) which
  11. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-e8c72fb28fe74ad09b574db465c5a1d1
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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