Sodium Thiosulfate → HCID 11165277, compound

HRID 749472Notes

Reaction equation

HRID 749472 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[CH3:29])[CH2:19][CH2:20][OH:21])[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[CH3:29])[CH2:19][CH:20]=[O:21])[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 689767833-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Product 1

HCID 11165277HCID 11165277, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide (350 mg, 0.89 mmol) was dissolved in CH2Cl2 (15 mL) together with Dess-Martin periodinane (410 mg, 098 mmol) and the mixture was stirred at room temperature for 4 h. Sodium thiosulfate (0.84 g, 5.2 mmol), dissolved in a saturated solution of NaHCO3 aq, was added and the mixture was then stirred vigorously for 1 h. The organic layer was washed with NaHCO3 aq and then brine. The solution was dried over Na2SO4 and the solvent was removed by evaporation. There was obtained 310 mg (89%) of 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil. 1H NMR (300 MHz, CDCl3): 1.0-4.5 (cm, 19H), 6.6-7.4 (cm, 5H), 9.8 (s, 1H). LCMS: m/z 391 (M−1)−.

Workup

  1. additionwas added
  2. stirringthe mixture was then stirred vigorously for 1 h
  3. washThe organic layer was washed with NaHCO3 aq
  4. dry with materialThe solution was dried over Na2SO4
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-7fa379df54db4cfba41e159893208fa9
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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