Trifluoroacetic acid → 4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]-1,2,3,6-tetrahydropyridine

HRID 2218897Notes

Reaction equation

HRID 2218897 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:26][C:24]1([CH3:27])[CH2:23][C:22]([CH3:28])([CH3:29])[CH2:21][CH:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597694334-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

Product 1

HCID 231421034-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]-1,2,3,6-tetrahydropyridineYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (570 mg, 1.43 mmol) produced in Example (102d) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL), followed by stirring for 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 430 mg of the title compound as a light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous solution of sodium hydrogencarbonate
  2. additionwas added to the obtained residue, and extraction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-0566c64501624febb95b4326dd558e26
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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