Triethylamine → 11beta-Fluoro-3-methoxyoestra-3,5-dien-17-one

HRID 650344Notes

Reaction equation

HRID 650344 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:21])[CH2:6][CH2:5]1.[C:22]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C>COC(OC)(C)C.C(OCC)(=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9](=[CH:10][CH2:11]2)[CH:8]=[C:7]([O:21][CH3:22])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1097914511beta-Fluorooestr-4-ene-3,17-dione

Product 1

HCID 1173826011beta-Fluoro-3-methoxyoestra-3,5-dien-17-one

Reagents, catalysts & solvents 2

HCID 64952,2-DimethoxypropaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.8 g of 11β-fluoro-estr-4-ene-3,17-dione is stirred in 40 ml of 2,2-dimethoxypropane with 780 mg of pyridinium-toluene4-sulfonate for 5 hours at 80° C. Then, 1.5 ml of triethylamine is added, it is diluted with ethyl acetate and washed with saturated sodium chloride solution. After crystallization from methanol, 5.3 g of 11β-fluoro-3-methoxy-estra-3,5-dien-17-one with a melting point of 173° C. is obtained.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customAfter crystallization from methanol, 5.3 g of 11β-fluoro-3-methoxy-estra-3,5-dien-17-one with a melting point of 173° C.
  3. customis obtained

Sources & evidence

ORD record
ord-c3074b20f77547998a0043470d06a4e9
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

Loading…