Trifluoroacetic acid → HCID 86600240, compound

HRID 859903Notes

Reaction equation

HRID 859903 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 for 9 hours under a hydrogen pressure of 3.9×105 Pa. The catalyst was collected from the reaction mixture by filtration and was washed with ethanol containing 25% water (300 mL). The filtrate and the washing solution were combined and the combined solution was concentrated under reduced pressure. The resultant pale brown crystal was suspended in tetrahydrofuran (100 mL) and was collected by filtration. The collected crystal was washed with tetrahydrofuran and was dried under reduced pressure to give 34.1 g of (3R,4R)-3-cyclopropylaminomethyl-4-methylpyrrolidine-trifluoroacetate as a white crystal.

Workup

  1. filtrationThe catalyst was collected from the reaction mixture by filtration
  2. washwas washed with ethanol containing 25% water (300 mL)
  3. concentrationthe combined solution was concentrated under reduced pressure
  4. filtrationwas collected by filtration
  5. washThe collected crystal was washed with tetrahydrofuran
  6. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-e77a049527e249d79e08b21a1e942163
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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