Potassium Fluoride → HCID 76567870, compound

HRID 1728152Notes

Reaction equation

HRID 1728152 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:37])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([C:30]#[C:31][Si](C)(C)C)[CH:27]=[CH:26][C:25]=3[OH:36])[C:5]2=[CH:4][CH:3]=1.[F-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:37])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([C:30]#[CH:31])[CH:27]=[CH:26][C:25]=3[OH:36])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 76568074HCID 76568074, compound

Product 1

HCID 76567870HCID 76567870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-hydroxy-5-(2-trimethylsilanyl-ethynyl)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′-dione was dissolved in methanol (10 mL). To the stirred solution, KF (Aldrich, 270 mg) was added and the mixture was stirred at rt overnight. The solvent was removed under reduced and the residue was treated with 6 mL of 5% MeOH in methylene chloride. The solid was filtered out and the filtrate was concentrated to about 2 mL and loaded on to an ISCO column. Chromatography (eluent with 5% MeOH in methylene chloride) gave a white solid. 30 mg. MS (H+), 477.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with 6 mL of 5% MeOH in methylene chloride
  3. filtrationThe solid was filtered out
  4. concentrationthe filtrate was concentrated to about 2 mL
  5. customChromatography (eluent with 5% MeOH in methylene chloride) gave a white solid

Sources & evidence

ORD record
ord-6f3dc5a172fb4a3dad3e5c7c70a2e449
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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