Sodium Chloride → HCID 69918825, compound

HRID 1838918Notes

Reaction equation

HRID 1838918 reaction equation
BrC[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][NH:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1.[Cl-].[Na+].[CH3:41]N1CCCC1=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][CH2:28][N:29]([CH3:41])[CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 13387N-methyl-2-pyrrolidoneHCID 158706647alpha-(5-Bromopentyl)-11beta-fluorooestra-1,3,5(10)-triene-3,17beta-diolHCID 22898654N-Methyl-2-(4-methylphenyl)ethan-1-amine

Product 1

HCID 69918825HCID 69918825, compound

Conditions

Temperature
80 °C

Procedure

660 mg of 7α-(5-bromopentyl)-11β-fluorooestra-1,3,5(10)-triene-3,17β-diol are dissolved in 10 ml of N-methylpyrrolidone, treated with 1.2 g of methyl-(2-p-tolylethyl)amine and stirred at a bath temperature of 80° C. for 3 hours. For work-up, the mixture is added to saturated sodium chloride solution, extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness in vacuo. Column-chromatographic purification on silica gel using an ethyl acetate-methanol-ammonia gradient and subsequent crystallization from ethyl acetate/methylene chloride/hexane yields 277 mg of 11β-fluoro-7α-{5-[methyl-(2-p-tolylethyl)amino]pentyl}oestra-1,3,5(10)-triene-3,17β-diol of melting point 142-143° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness in vacuo
  4. customColumn-chromatographic purification on silica gel using
  5. customan ethyl acetate-methanol-ammonia gradient and subsequent crystallization from ethyl acetate/methylene chloride/hexane

Sources & evidence

ORD record
ord-adf50849842543e4ad189cbc949043ba
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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