Water → p-Toluenesulfonic acid

HRID 1023819Notes

Reaction equation

HRID 1023819 reaction equation
COCCOC[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:16][C@H:15]2[NH2:17])=[CH:10][CH:9]=1.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1.O.[OH-].[Na+].O>CCO>[NH2:17][C@@H:15]1[CH2:16][C@H:14]1[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 67064933(trans)-2-(4-((2-Methoxyethoxy)methoxy)phenyl)cyclopropanamine2×

Product 2

HCID 6101p-Toluenesulfonic acidHCID 128670rel-4-((1R,2S)-2-Aminocyclopropyl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (trans)-2-(4-((2-methoxyethoxy)methoxy)phenyl)cyclopropanamine (Intermediate L, 62 mg, 0.26 mmol) and p-TsOH.H2O (60 mg, 0.31 mmol) in EtOH (5 mL) was heated at 75° C. for 2 h. The pH of the reaction was adjusted to 7 with NaOH (10% aqueous solution), the mixture was poured into water (10 mL) and extracted with EtOAc (4×10 mL). The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent a brownish residue was obtained (44 mg, 4-((trans)-2-aminocyclopropyl)phenol contaminated with p-TsOH) that was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc (4×10 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent a brownish residue

Sources & evidence

ORD record
ord-e1b18015bf364c3b96c268bc4c2bcfbd
Source dataset
uspto-grants-2014_05
Patent number
US08722743B2

Reaction notes

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