HCID 86690349, compound → HCID 71226842, compound

HRID 2409922Notes

Reaction equation

HRID 2409922 reaction equation
[CH3:1][C@:2]1([NH:18]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH2:3]1>CO.[Pd]>[CH3:1][C@:2]1([NH2:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 86690349HCID 86690349, compound

Product 1

HCID 71226842HCID 71226842, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-benzyl (3-methyl-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)carbamate (2.05 g, 5.22 mmol) in MeOH (20 mL) was added palladium on carbon (0.406 g, 3.81 mmol) under nitrogen atmosphere. The resultant black color suspension was stirred under hydrogen balloon pressure at rt for 2 hours. The reaction mass was filtered on Celite, the filter cake was washed with methanol (3×10 mL), and combined filtrate was concentrated and dried under vacuum to get 1.6 g of crude compound. This crude was purified on a 12 g silica cartridge by ISCO, eluted the compound around 5% methanol in chloroform. Pure fractions were collected and concentrated to get (S)-3-methyl-1-(4-(trifluoromethyl)phenyl)piperidin-3-amine (570 mg, 1.493 mmol, 28.6% yield) as pale yellow gummy solid.

Workup

  1. filtrationThe reaction mass was filtered on Celite
  2. washthe filter cake was washed with methanol (3×10 mL)
  3. concentrationwas concentrated
  4. customdried under vacuum
  5. customto get 1.6 g of crude compound
  6. customThis crude was purified on a 12 g silica cartridge by ISCO
  7. washeluted the compound around 5% methanol in chloroform
  8. customPure fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9cb0dfb615f440c8aaa0fda8001b4995
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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