Ammonia → HCID 69916213, compound

HRID 1263735Notes

Reaction equation

HRID 1263735 reaction equation
[CH2:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16][C:17](=[O:21])[CH:18]=2)[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH:6]=1)[CH3:2].[Li].N.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C@@H:3]1[CH2:20][C@@H:19]2[C@H:14]([CH2:15][CH2:16][C:17](=[O:21])[CH2:18]2)[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 9839314HCID 9839314, compound

Product 1

HCID 69916213HCID 69916213, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of (7α,17β)-7-ethyl-17-hydroxyestra-4,14-dien-3-one (Example 1a; 0.67 g) in dry tetrahydrofuran (13 ml) was added to a refluxing solution of lithium (0.31 g) in liquid ammonia (44 ml). After 30 min. stirring at −40° C., solid ammonium chloride was added and the ammonia was allowed to evaporate. Water was added and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of ammonium chloride and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (5α,7α,17β)-7-ethyl-17-hydroxyestr-14-en-3-one (0.21 g), 1H-NMR (CDCl3) δ5.02 (s, 1 H), 3.98 (t, 1 H, J=8.4 Hz), 0.99 (s, 3 H), 0.89 (t, 3 H,J=7.5 Hz).

Workup

  1. customto evaporate
  2. additionWater was added
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined organic phases were washed with a saturated aqueous solution of ammonium chloride and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed7ec6df6afe4a15a2f64ba312fd1bd0
Source dataset
uspto-grants-2003_04
Patent number
US06541465B2

Reaction notes

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