Sodium Bicarbonate → (+/-)-4-[1-(5,6-Diphenylpyrazin-2-yl)pyrrolidin-2-yl]-1-butanol

HRID 1271277Notes

Reaction equation

HRID 1271277 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH2:24][CH2:25][CH2:26][CH2:27][O:28]C3CCCCO3)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 22931951(+/-)-1-[1-(5,6-Diphenylpyrazin-2-yl)pyrrolidin-2-yl]-4-(2-tetrahydropyranyloxy)butane

Product 1

HCID 18452667(+/-)-4-[1-(5,6-Diphenylpyrazin-2-yl)pyrrolidin-2-yl]-1-butanolYield 107.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.25 g of (±)-1-[1-(5,6-diphenylpyrazin-2-yl)pyrrolidin-2-yl]-4-(2-tetrahydropyranyloxy)butane in 13 ml of methanol, 0.52 g of p-toluenesulfonic acid monohydrate was added, followed by stirring at room temperature for 3 hours. The reaction solution was alkalified by adding an aqueous saturated sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain 1.10 g of the desired compound as a pale yellow oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7c34754af254a2e9272709fe1e0424b
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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