Heptanoyl chloride → 11beta-Fluoro-17beta-heptanoyloxy-7alpha-methylestr-4-en-3-one

HRID 900677Notes

Reaction equation

HRID 900677 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.[C:23](Cl)(=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>O1CCCC1.N1C=CC=CC=1>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[O:20][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 17313Heptanoyl chlorideHCID 516892Sodium BicarbonateHCID 990463811beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-one

Product 1

HCID 1027353411beta-Fluoro-17beta-heptanoyloxy-7alpha-methylestr-4-en-3-one

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 220 mg of 11β-fluoro-17β-hydroxy-7α-methylestr-4-ene-3-one (I) in 5 ml of tetrahydrofuran and 1.09 ml of pyridine was mixed drop by drop at 0° C. with 1.09 ml of heptanoyl chloride and stirred for 1 hour. Then, it was mixed with sodium bicarbonate solution, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 210 mg of pure 11β-fluoro-17β-heptanoyloxy-7α-methylestr-4-en-3-one (I′) was obtained as a foam ([α]D20=+40.8° (c=0.56% in chloroform)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-3593b9f7a35147caa0ce76076569c79e
Source dataset
uspto-grants-2008_04
Patent number
US07361645B2

Reaction notes

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