Methylamine → 11beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-one

HRID 650377Notes

Reaction equation

HRID 650377 reaction equation
[CH3:1][NH2:2].[F:3][C@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][C:18]2=[O:22])[C@H:14]2[C@H:5]1[C:6]1[CH:7]=[CH:8][C:9]([OH:29])=[CH:10][C:11]=1[CH2:12][C@H:13]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]I>O1CCCC1>[F:3][C@H:4]1[CH2:21][C@@:19]2([CH3:20])[C@@H:15]([CH2:16][CH2:17][C:18]2=[O:22])[C@H:14]2[C@H:5]1[C:6]1[CH:7]=[CH:8][C:9]([OH:29])=[CH:10][C:11]=1[CH2:12][C@H:13]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15870673HCID 15870673, compound

Product 1

HCID 1587066511beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-oneYield 123.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.1 g of methylamine is condensed in a solution of 6.8 g of 11β-fluoro-3-hydroxy-7α-(5-iodopentyl)-estra-1,3,5(10)-trien-17-one in 35 ml of anhydrous tetrahydrofuran at −78° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −20° C., it was allowed to reach room temperature to be able to evaporate excess methylamine. Then, the reaction solution is added to saturated sodium bicarbonate solution, extracted 3 times with ethyl acetate, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 6.7 g of 11β-fluoro-3-hydroxy-7α-[5-(methylamino)-pentyl]-estra-1,3,5(10)-trien-17-one is obtained as crude product.

Workup

  1. customwas opened at −20° C.
  2. customto reach room temperature
  3. customto evaporate excess methylamine
  4. additionThen, the reaction solution is added to saturated sodium bicarbonate solution
  5. extractionextracted 3 times with ethyl acetate
  6. customdried on magnesium sulfate
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-6b4372d79d4f4a12821ff7cda687a631
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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