HCID 71233209, compound → HCID 71233212, compound

HRID 2409923Notes

Reaction equation

HRID 2409923 reaction equation
[CH3:1][C@:2]1([NH:18][C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[NH:25]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([NH:18][C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[NH2:25])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][CH:9]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 71233209HCID 71233209, compound

Product 1

HCID 71233212HCID 71233212, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl ((1R,2R)-2-(((S)-3-methyl-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)amino)cyclohexyl)carbamate (420 mg, 0.858 mmol) in MeOH (4 mL) was added palladium on carbon (10%) (84 mg, 0.789 mmol) under nitrogen atmosphere. The resultant black color suspension was stirred under hydrogen balloon pressure at RT for 2 h. The reaction mass was filtered on Celite and the filter cake was washed with methanol (3×5 mL). The filtrate was concentrated and dried under vacuum to get (1R,2R)—N1-((S)-3-methyl-1-(4-(trifluoromethyl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine (300 mg, 0.667 mmol, 78% yield) as off white solid. This was directly used for next reaction with out any further purification. Anal. Calcd. for C19H28F3N3 m/z 355.4, found: 490.4 (M+H)+; This was taken for next step with out any further characterization.

Workup

  1. filtrationThe reaction mass was filtered on Celite
  2. washthe filter cake was washed with methanol (3×5 mL)
  3. concentrationThe filtrate was concentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1d3f0eb220fb445a8e087a717f610510
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

Loading…