Ethanolamine → (2beta,3alpha,5alpha)-3-Hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one

HRID 233493Notes

Reaction equation

HRID 233493 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([N:22]2[CH2:27][CH2:26][O:25][C:24]([CH3:29])([CH3:28])[CH2:23]2)[CH2:20][C@@:19]2([CH3:30])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:31])[CH2:16][C@@:15]2([CH3:32])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=O)[CH3:13])[CH2:3]1.[NH2:33][CH2:34][CH2:35][OH:36].C1(C)C=CC=CC=1>O>[OH:1][C@@H:2]1[C@@H:21]([N:22]2[CH2:27][CH2:26][O:25][C:24]([CH3:29])([CH3:28])[CH2:23]2)[CH2:20][C@@:19]2([CH3:30])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:31])[CH2:16][C@@:15]2([CH3:32])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[N:33][CH2:34][CH2:35][OH:36])[CH3:13])[CH2:3]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 1140TolueneHCID 9803583Org-21465

Product 1

HCID 86750168(2beta,3alpha,5alpha)-3-Hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (8.0 g), 2-aminoethanol (40 ml), toluene (200 ml) and Dowex 50-W resin (0.8 g) were added to a flask fitted with a water separator. The mixture was heated under reflux for 10 h, by which time approximately 15 ml of a distillate had collected in the water separator. The contents of the flask were filtered while still hot and the residue was rinsed with hot toluene. The filtrate was washed with water, dried over sodium sulfate and the solvent was removed under reduced pressure to give (2β,3α,5α)-3-hydroxy-20-[(2-hydroxyethyl)imino]-2-(2,2-dimethyl-4-morpholinyl)pregnan-11-one. δ (CDCl3) 0.50 (s,3H), 1.05 (s,3H), 1.21 (s,3H), 1.23 (s,3H) and 2.36 (s,2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 10 h, by which time approximately 15 ml of a distillate
  3. customhad collected in the water separator
  4. filtrationThe contents of the flask were filtered while still hot and the residue
  5. washwas rinsed with hot toluene
  6. washThe filtrate was washed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c1b23e85994947aeb8f35be28240fe07
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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