Water → HCID 15858642, compound

HRID 1603363Notes

Reaction equation

HRID 1603363 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[CH:22]=[C:21]([OH:25])[CH:20]=[CH:19][C:18]=2[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][C@@H:16]2[F:26])([CH3:14])[C@@H:12]([OH:27])[CH2:11][CH2:10]1.[CH3:28][NH2:29].O>CN(C)C=O>[F:26][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH:27])[C@H:8]2[C@H:17]1[C:18]1[CH:19]=[CH:20][C:21]([OH:25])=[CH:22][C:23]=1[CH2:24][C@H:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:29][CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 158706647alpha-(5-Bromopentyl)-11beta-fluorooestra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 15858642HCID 15858642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g of 7α-(5-bromopentyl)-11β-fluoro-estra-1,3,5(10)-triene-3,17β-diol in 20 ml of dimethylformamide is stirred with 8 ml of a 40% aqueous methylamine solution for 3.5 hours at 80° C. Then, it is added to water, extracted three times with ethyl acetate, washed with water and common salt solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 1.77 g of 11β-fluoro-7α-[5-(methylamino)-pentyl]-estra-1,3,5(10)-triene-3,17β-diol is obtained.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with water and common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-3089e7b22429456dad2df98214c6005b
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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