Ammonia → HCID 69913587, compound

HRID 353704Notes

Reaction equation

HRID 353704 reaction equation
[CH3:1][C:2]([Si:5]([CH3:30])([CH3:29])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C:13]3[C@H:14]([CH2:27][OH:28])[CH2:15][C:16]4[CH:17]=[C:18]([O:25][CH3:26])[CH:19]=[CH:20][C:21]=4[C:22]=3[CH2:23][CH2:24][C@:8]12[CH3:9])([CH3:4])[CH3:3].N.[Li].[Cl-].[NH4+]>O1CCCC1.C(O)C>[CH3:4][C:2]([Si:5]([CH3:30])([CH3:29])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH2:20][CH:19]=[C:18]([O:25][CH3:26])[CH2:17][C:16]=1[CH2:15][C@H:14]3[CH2:27][OH:28])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 15692363HCID 15692363, compound

Product 1

HCID 69913587HCID 69913587, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

i)—A solution of (7α,17β)-17-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyestra-1,3,5(10),8-tetraene-7-methanol [Kuenzer, H. et al, Tetrahedron Lett. 32, 743 (1991); 7.3 g] in dry tetrahydrofuran (100 ml) was added to liquid ammonia (400 ml), cooled at −40° C. Lithium granulate (3.58 g) was added and the reaction mixture was stirred at reflux temperature for 1 h. Ethanol (22.1 ml) was added carefully and the mixture was stirred for 30 min. 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 water and brine, dried over magnesium sulfate and concentrated under reduced pressure, to give (7α,17β)-17-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyestra-2,5(10)-diene-7-methanol (7.22 g). The product was used in the following step without further purification.

Workup

  1. temperatureat reflux temperature for 1 h
  2. stirringthe mixture was stirred for 30 min
  3. customto evaporate
  4. additionWater was added
  5. extractionthe product was extracted into ethyl acetate
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-092a9df55bc0488bb77cd2ab7f577812
Source dataset
uspto-grants-2004_06
Patent number
US06756366B1

Reaction notes

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