Acetic Acid → HCID 23141598, compound

HRID 2218911Notes

Reaction equation

HRID 2218911 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH:15]=2)=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[CH:24](=O)[CH2:25][CH2:26][CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:24]([N:11]1[CH2:10][CH2:9][CH:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH:15]=2)[CH2:13][CH2:12]1)[CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231425804-[5-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine

Product 1

HCID 23141598HCID 23141598, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine (70 mg, 0.22 mmol) produced in Example (106g) in tetrahydrofuran (2 mL) were added butyraldehyde (19.2 mg, 0.27 mmol), sodium triacetoxyborohydride (71 mg, 0.33 mmol) and acetic acid (27 mg, 0.44 mmol), followed by stirring for 15 hours at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated under reduced pressure to give a residue, which was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 55 mg of 1-butyl-4-[5-fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperidine as a light yellow oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue, which
  4. customwas purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-5c8336d0cddb489c83838f2043735b51
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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