Acetic Acid → 1-(1,1-Dimethylethyl) 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

HRID 1901077Notes

Reaction equation

HRID 1901077 reaction equation
C([O:8][C:9](=[O:31])[C:10]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)C1C=CC=CC=1.C(O)(=O)C>[Pd].CO>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])([C:9]([OH:31])=[O:8])[CH2:15][CH2:14]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 54269290HCID 54269290, compound

Product 1

HCID 211933131-(1,1-Dimethylethyl) 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(2-methylbenzyl) N-t-butoxycarbonyl isonipecotic acid benzyl ester (2.36 g, 5.57 mmol), 5% Palladium on charcoal catalyst (250 mg), and glacial acetic acid (3 ml) in methanol (75 ml), was hydrogenated at 51 p.s.i. overnight, in a Parr shaker. The reaction mixture was then filtered through a pad of Celite and the pad washed several times with methanol. The combined filtrates were then concentrated in vacuo to the product, a white solid. 30 mg of this material was recrystallized from toluene to afford fine white crystals m.p. 176°-179° C. dec.

Workup

  1. customovernight
  2. filtrationThe reaction mixture was then filtered through a pad of Celite
  3. washthe pad washed several times with methanol
  4. concentrationThe combined filtrates were then concentrated in vacuo to the product
  5. custom30 mg of this material was recrystallized from toluene

Sources & evidence

ORD record
ord-439b22cc54dc459ebff23793c89a656b
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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