HCID 9879259, compound → HCID 118105538, compound

HRID 2200367Notes

Reaction equation

HRID 2200367 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:12]2)C1C=CC=CC=1>CO.[Pd]>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:11]2[CH2:10][C@H:9]3[NH:8][C@H:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 9879259HCID 9879259, compound

Product 1

HCID 118105538HCID 118105538, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To the stirred solution of 8-benzyl-3-(4-fluorophenyl)-3,8-diazabicyclo[3.2.1]octane (3.5 g, 11.81 mmol) in methanol (30 ml) was added 10% palladium on charcoal (100 mg, 0.940 mmol) at 25° C. The reaction mixture was stirred under hydrogen atmosphere for 3-4 h at 40° C. The reaction mixture was then cooled to 25° C. and filtered through a celite bed. The celite bed was washed with methanol (2×25 ml). The combined filtrate was concentrated under reduced pressure to obtain title compound (2.3 g, 94%).

Workup

  1. temperatureThe reaction mixture was then cooled to 25° C.
  2. filtrationfiltered through a celite bed
  3. washThe celite bed was washed with methanol (2×25 ml)
  4. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e2b494bb9e2447c9abeca9a14dfe390
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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