Trifluoroacetic acid → HCID 86600240, compound

HRID 2108799Notes

Reaction equation

HRID 2108799 reaction equation
C([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([CH2:14][NH:15][CH:16]2[CH2:18][CH2:17]2)[CH2:9]1)C1C=CC=CC=1.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(O)C.[C].[Pd]>[CH:16]1([NH:15][CH2:14][C@@H:10]2[C@@H:11]([CH3:13])[CH2:12][NH:8][CH2:9]2)[CH2:17][CH2:18]1.[F:19][C:20]([F:25])([F:24])[C:21]([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66704854HCID 66704854, compound

Product 1

HCID 86600240HCID 86600240, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(3S,4R)-1-Benzyl-3-cyclopropylaminomethyl-4-methylpyrrolidine (25.0 g) was dissolved in ethanol (200 mL). To this solution, trifluoroacetic acid (15.7 mL) and 10% palladium carbon (12.5 g) were added and the mixture was stirred at room temperature under hydrogen pressure of 3.9×105 Pa for 9 hours. The catalyst in the reaction mixture was filtered and the collected catalyst was washed with a 25% aqueous ethanol (300 mL). The filtrate and the washings were combined and concentrated under reduced pressure. The remaining pale brown crystals were suspended in tetrahydrofuran (100 mL) and were filtered. The collected crystals were washed with tetrahydrofuran and dried under reduced pressure to give (3R,4R)-3-cyclopropylaminomethyl-4-methylpyrrolidine-trifluoroacetate as white crystals (34.1 g).

Workup

  1. filtrationThe catalyst in the reaction mixture was filtered
  2. washthe collected catalyst was washed with a 25% aqueous ethanol (300 mL)
  3. concentrationconcentrated under reduced pressure
  4. filtrationwere filtered
  5. washThe collected crystals were washed with tetrahydrofuran
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-70e4df8f00f8459bb71a84e20c327f93
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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