HCID 23141613, compound → HCID 23142803, compound

HRID 2218899Notes

Reaction equation

HRID 2218899 reaction equation
[ClH:1].[CH2:2]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]>CO.[Pd]>[ClH:1].[CH2:2]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([CH3:26])([CH3:27])[CH2:19]2)[CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 23141613HCID 23141613, compound

Product 1

HCID 23142803HCID 23142803, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-butyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-1,2,3,6-tetrahydropyridine hydrochloride (48 mg, 0.12 mmol) produced in Example (102f) in methanol (3 mL) was added 10% palladium on carbon (100 mg, wet), followed by stirring for 4 hours at room temperature and atmospheric pressure under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. Ether and hexane were added to the obtained residue to produce a solid, which was then triturated by sonication. The solid was filtered and dried under reduced pressure to give 9 mg of the title compound as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionEther and hexane were added to the obtained residue
  4. customto produce a solid, which
  5. customwas then triturated by sonication
  6. filtrationThe solid was filtered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-fce9f67a52da4ce18d3fc2687c52c782
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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