Methanesulfonic Acid → 3-Cyclopropylamino-3-methylazetidine dimethanesulphonate

HRID 743661Notes

Reaction equation

HRID 743661 reaction equation
C([N:14]1[CH2:17][C:16]([NH:19][CH:20]2[CH2:22][CH2:21]2)([CH3:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:23][S:24]([OH:27])(=[O:26])=[O:25]>CO.[OH-].[OH-].[Pd+2]>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[CH:20]1([NH:19][C:16]2([CH3:18])[CH2:17][NH:14][CH2:15]2)[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 194237611-Benzhydryl-3-cyclopropylamino-3-methylazetidine

Product 1

HCID 194237343-Cyclopropylamino-3-methylazetidine dimethanesulphonateYield 57.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

14.5 g of 1-benzhydryl-3-cyclopropylamino-3-methyl-azetidine in 150 cm3 of methanol are hydrogenated at atmospheric pressure and at a temperature in the region of 20° C. for 1 hour in the presence of 5.6 g of 20% palladium hydroxide on carbon. The reaction mixture is treated with 10 g of methanesulphonic acid. After removal of the catalyst by filtration and concentration to dryness under reduced pressure (20 kPa) at approximately 40° C., the residue is washed with 3 times 150 cm3 of ethyl ether. The final residue is taken up with 100 cm3 of 2-propanol, drained and washed with twice 50 cm3 of acetone. 9.1 g of 3-cyclopropylamino-3-methylazetidine dimethanesulphonate are obtained in the form of a colorless solid, melting point 136° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration and concentration to dryness under reduced pressure (20 kPa) at approximately 40° C.
  3. washthe residue is washed with 3 times 150 cm3 of ethyl ether
  4. washwashed with twice 50 cm3 of acetone

Sources & evidence

ORD record
ord-118a0d32535e4d1bab9d8dd739c9ea16
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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