Sodium Chloride → HCID 69916466, compound

HRID 1837267Notes

Reaction equation

HRID 1837267 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:4]1[CH:5]=[CH:6][C:7]([OH:27])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]I.[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][NH:39][CH3:40])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[Na+]>CN1CCCC1=O>[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:40])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:11]1[CH2:10][C:9]2[CH:8]=[C:7]([OH:27])[CH:6]=[CH:5][C:4]=2[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:2]2[F:1])([CH3:18])[C@@H:16]([OH:20])[CH2:15][CH2:14]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 23497039N-Methyl-3-(phenylmethoxy)-1-propanamineHCID 6991842711beta-Fluor-7alpha-(5-iodopentyl)-estra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 69916466HCID 69916466, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 486 mg of 11β-fluor-7α-(5-iodopentyl)-estra-1,3,5(10)-triene-3,17β-diol in 10 ml of 1-methyl-2-pyrrolidinone is stirred with 540 mg of (3-benzyloxy-propyl)-methyl-amine for 3 hours at a bath temperature of 80° C. Then, the batch is added to saturated sodium chloride solution, extracted with ether, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with methylene chloride/methanol/ammonia. 237 mg of 7α-{5-[(3-benzyloxy-propyl)-methyl-amino]-pentyl}-11β-fluor-estra-1,3,5(10)-triene-3,17β-diol is obtained as a foam [α]D=+48° (c=0.5 in CHCl3).

Workup

  1. extractionextracted with ether
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with methylene chloride/methanol/ammonia

Sources & evidence

ORD record
ord-3671d13f5c5a43388e3264aa32b79b52
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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