p-Toluenesulfonic acid → HCID 67534555, compound

HRID 494889Notes

Reaction equation

HRID 494889 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.CC1C=CC(S(O[CH2:23][CH2:24][C:25]2[S:26][C:27]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:28]=3[CH:29]=2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[CH3:41][C@@H:42]1[CH2:46][CH2:45][CH2:44][NH:43]1.C(#N)C>>[Br:34][C:31]1[CH:32]=[CH:33][C:27]2[S:26][C:25]([CH2:24][CH2:23][N:43]3[CH2:44][CH2:45][CH2:46][C@H:42]3[CH3:41])=[CH:29][C:28]=2[CH:30]=1

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 641544(R)-2-MethylpyrrolidineHCID 22274441HCID 22274441, compound

Product 1

HCID 67534555HCID 67534555, compoundYield 73.3%

Conditions

Temperature
55 °C

Procedure

Toluene-4-sulfonic acid, the product from Example 165D (0.45 g), and K2CO3 (0.23 g, 1.5 eq) was treated with a solution of (2R)-2-methylpyrrolidine solution in acetonitrile (11.1 g, 12.6 mg/g of solution, 1.5 eq). The mixture was heated at 55° C. for 24 hours, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was dissolved in 30 mL EtOAc, washed with 2×10 mL water, concentrated, and the residue was purified by column chromatography (silica gel, 10:90 MeOH:CHCl3) to provide the title compound as an oil (0.26 g, 73.3%). 1HNMR (CDCl3, δ) 1.10 (d, 3H), 1.4-2.0 (m, 4H), 2.20 (q, 1H), 2.30-2.50 (m, 2H), 3.00-3.23 (m, 4H), 6.97 (s, 1H), 7.33 (d of d, 1H), 7.60 (d, 1H), 7.78 (d, 1H). MS (m/z): 324, 326 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 30 mL EtOAc
  4. washwashed with 2×10 mL water
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (silica gel, 10:90 MeOH:CHCl3)

Sources & evidence

ORD record
ord-9dee9ded36b54959b53eff9428ce6ed2
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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