Hydrochloric Acid → (S)-3-[(R)-1-(3-methoxyphenyl)ethylamino]pyrrolidine dihydrochloride

HRID 1811643

Reaction equation

HRID 1811643 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH3:15])[CH2:9]1)C1C=CC=CC=1.[ClH:24]>CO.O1CCOCC1.[OH-].[Pd+2].[OH-]>[ClH:24].[ClH:24].[CH3:23][O:22][C:18]1[CH:17]=[C:16]([C@H:14]([NH:13][C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH3:15])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58973545(S)-(1-benzylpyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine

Product 1

HCID 67408353(S)-3-[(R)-1-(3-methoxyphenyl)ethylamino]pyrrolidine dihydrochloride

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.67 g of (S)-(1-benzylpyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine dissolved in 100 ml of methanol were added 830 mg of palladium hydroxide and 8.85 ml of a solution of 4M hydrochloric acid in dioxane, and the mixture was shaked under hydrogen atmosphere at 3 atm at room temperature for 3 days. Palladium hydroxide was removed, and the solvent was evaporated. To the residue was added methanol, and the resulting precipitates were collected by filtration, washed with methanol and dried to obtain 1.14 g of (S)-3-[(R)-1-(3-methoxyphenyl)ethylamino]pyrrolidine dihydrochloride (the following Reference example Table, Reference example 1.001).

Workup

  1. customPalladium hydroxide was removed
  2. customthe solvent was evaporated
  3. additionTo the residue was added methanol
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-6e9fee769062453794fd522f467877a0
Source dataset
uspto-grants-2013_01
Patent number
US08362274B2

Linked notes

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