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

HRID 1576774Notes

Reaction equation

HRID 1576774 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@H:13]([OH:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.O1CCCC1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CCOCC>[OH:24][C@@H:13]1[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@@H: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])[CH2:2][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH2:12]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (1.6 g) in refluxing tetrahydrofuran (40 ml) was treated with morpholine (0.7 ml) under nitrogen for 3 hr and then poured into ether. The ethereal solution was washed successively with 5% aqueous sodium bicarbonate and water, dried (Na2SO4) and evaporated. The residue was partitioned between a mixture of 2N-hydrochloric acid (6 ml), water (200 ml), acetone (20 ml) and methylene chloride (120 ml). The aqueous phase was treated with 2N-sodium hydroxide (6 ml) and sodium chloride (20 g) and the resulting mixture was extracted with methylene chloride. The extracts were washed with water, dried (Na2SO4) and evaporated to give title compound (1.5 g) as a white foam, [α]D + 81° (c 1.1).

Workup

  1. washThe ethereal solution was washed successively with 5% aqueous sodium bicarbonate and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was partitioned between a mixture of 2N-hydrochloric acid (6 ml), water (200 ml), acetone (20 ml) and methylene chloride (120 ml)
  5. additionThe aqueous phase was treated with 2N-sodium hydroxide (6 ml) and sodium chloride (20 g)
  6. extractionthe resulting mixture was extracted with methylene chloride
  7. washThe extracts were washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-e8b8c65bde8742daba317fad8265776f
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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