Methanol → HCID 53856125, compound

HRID 863586Notes

Reaction equation

HRID 863586 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:6]=1[CH2:13][NH:14][C@H:15]1[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[C@H:16]1[CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OOS([O-])=O.[K+].[OH-:42].[Na+].C[OH:45]>O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:12])(=[O:45])=[O:42])=[CH:7][C:6]=1[CH2:13][NH:14][C@H:15]1[CH:20]2[CH2:19][CH2:18][N:17]([CH2:22][CH2:21]2)[C@H:16]1[CH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23707502Potassium hydroxy sulfiteHCID 70197397HCID 70197397, compound

Product 1

HCID 53856125HCID 53856125, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and ice-cooled solution of (2S,3S)-N-(2-methoxy-5-methylthiophenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride in methanol (25 mL) was added a solution of oxone (2.41 g) in water (25 mL). The reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was basified to pH 10-11 with 1N NaOH aq. solution with ice-cooling, and extracted with CHCl3 (80 mL×4). The combined organic layers were washed with brine (80 mL), dried (MgSO4) and concentrated in vacuo to give crude (2S,3S)-N-(2-methoxy-5-methylsulfonylphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (white soap, 1.49 g). The residue was purified by chromatography on silica gel (60 g) with chloroform-methanol (20:1-10:1) to give (2S,3S)-N-(2-methoxy-5-methylsulfonylphenyl)methyl-2-diphenylmethyl-1-azabicyclo[2.2.2]octan-3-amine (1.08 g, 79%) as a white amorphous solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  2. temperaturecooling
  3. extractionextracted with CHCl3 (80 mL×4)
  4. washThe combined organic layers were washed with brine (80 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e77e35b39c1468cab18fe7c5d5d7749
Source dataset
uspto-grants-1998_02
Patent number
US05721255

Reaction notes

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