Sulfuric acid magnesium salt (1:1) → HCID 57458887, compound

HRID 8635Notes

Reaction equation

HRID 8635 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][C@@H:4]([O:7][C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[C:17]([F:20])([F:19])[F:18])[CH2:3]1.[H][H].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)(=O)C.[Pt]>[CH3:1][N:2]1[CH2:6][CH2:5][C@@H:4]([O:7][C:8]2[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=2[C:17]([F:18])([F:19])[F:20])[CH2:3]1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 57437881(r)-1-Methyl-3-(3-nitro-6-trifluoromethylphenoxy)-pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 57458887HCID 57458887, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-nitrobenzotrifluoride (7.8 g, 26.9 mmol) in ethyl acetate (50 ml) was treated with 10% platinum on carbon (200 mg) then subjected to 40 psi hydrogen pressure for 3 hrs. The slurry was treated with anhydrous magnesium sulfate (5 g) then filtered through a pad of Celite. The filter cake was rinsed with ethyl acetate (2×25 ml) then the filtrate was evaporated under reduced pressure to an oil. This oil was evaporated twice for dichloromethane (50 ml) to remove trapped ethyl acetate. This gave the product as a clear light brown oil that solidified on standing (6.9 g, 99%): LCMS 249 (M++H).

Workup

  1. filtrationthen filtered through a pad of Celite
  2. washThe filter cake was rinsed with ethyl acetate (2×25 ml)
  3. customthe filtrate was evaporated under reduced pressure to an oil
  4. customThis oil was evaporated twice for dichloromethane (50 ml)
  5. customto remove

Sources & evidence

ORD record
ord-6bc67ca7fb6f48d4b4d2e9c4d8a61c2c
Source dataset
uspto-grants-2006_08
Patent number
US07091204B2

Reaction notes

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