Hydrochloric Acid → 1-(3-Azetidinyl)-3-pyrrolidinol dihydrochloride

HRID 749437Notes

Reaction equation

HRID 749437 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]3)[CH2:9]2)C=CC=CC=1.[ClH:24]>C(O)C.[Pd].[OH-].[OH-].[Pd+2]>[ClH:24].[ClH:24].[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]2)[CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 689780803-Pyrrolidinol, 1-[1-(diphenylmethyl)-3-azetidinyl]-

Product 1

HCID 689769631-(3-Azetidinyl)-3-pyrrolidinol dihydrochlorideYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-[1-(Diphenylmethyl)azetidin-3-yl]pyrrolidin-3-ol (310 mg, 0.98 mmol) was dissolved in ethanol (20 mL). A mixture of palladium hydroxide on carbon and palladium on activated carbon was added and to the resultant mixture was then added concentrated HCl (0.1 mL) dropwise. The mixture was stirred under hydrogen (5 atm) at room temperature overnight and then the catalyst was filtered off by means of Celite®. The solvent was removed by evaporation and the residue triturated with CH2Cl2. There was obtained 154 mg (79%) of 1-azetidin-3-ylpyrrolidin-3-ol dihydrochloride as a solid. 13C NMR (75 MHz, D2O): 48.8 (s), 65.1 (s), 67.7 (s), 70.9 (s), 76.2 (s), 85.7 (s); LCMS: m/z 143 (M+1)+.

Workup

  1. filtrationthe catalyst was filtered off by means of Celite®
  2. customThe solvent was removed by evaporation
  3. customthe residue triturated with CH2Cl2

Sources & evidence

ORD record
ord-1e1a7bc0b2a24385a402fc86930e4e9e
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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