Sodium Chloride → HCID 15858646, compound

HRID 1838912Notes

Reaction equation

HRID 1838912 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:4]1[CH:5]=[CH:6][C:7]([OH:43])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:42])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37].[BH4-].[Na+].[Cl-].[Na+]>C(O)C>[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:43])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:42])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:40])([F:41])[C:36]([F:37])([F:38])[F:39]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 8658764311beta-Fluoro-3-hydroxy-7alpha-{6-[methyl-(8,8,9,9,9-pentafluorononyl)-amino]hexyl}oestra-1,3,5(10)-trien-17-one

Product 1

HCID 15858646HCID 15858646, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

89 mg of 11β-fluoro-3-hydroxy-7α-{6-[methyl-(8,8,9,9,9-pentafluorononyl)amino]hexyl}oestra-1,3,5(10)-trien-17-one are dissolved in 2 ml of ethanol and treated with 22 mg of sodium borohydride. After stirring at room temperature for 1 hour, the solvent is for the most part stripped off in vacuo, the residue is treated with sodium chloride solution, and the mixture is extracted 3 times with methylene chloride, dried over magnesium sulphate and concentrated in vacuo. Preparative thin-layer chromatography using methylene chloride/methanol=9/1 as an eluent leads to 53 mg of 11β-fluoro-7x-{5-[methyl-(8,8,9,9,9-pentafluorononyl)amino]hexyl}oestra-1,3,5(10)-triene-3,17β-diol are obtained as a foam, [α]D=+32° (c=1.0 in chloroform).

Workup

  1. extractionthe mixture is extracted 3 times with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customare obtained as a foam, [α]D=+32° (c=1.0 in chloroform)

Sources & evidence

ORD record
ord-1703c158b8104733a66b949bed1ab26c
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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