1-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate → Ethyl 3-methylpiperidine-3-carboxylate

HRID 2370026Notes

Reaction equation

HRID 2370026 reaction equation
[CH3:1][C:2]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][CH2:6][CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1>C(OCC)(=O)C.CO.[Pd]>[CH3:1][C:2]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1

Participants

5

Reactant 1

HCID 534862661-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 18419721Ethyl 3-methylpiperidine-3-carboxylateYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.945 g, 12.92 mmol) and 5% Pd/C (800 mg) in ethyl acetate (20 mL) and methanol (20.00 mL) was vigorously stirred under a hydrogen balloon for 1.5 hr. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to dryness to give the desired crude product ethyl 3-methylpiperidine-3-carboxylate (2.010 g, 11.74 mmol, 91% yield) as a colorless oily residue. Anal. Calcd. for C9H17NO2 m/z 171.2, found: 172.2 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 4.25-4.06 (m, 2H), 3.31 (d, J=13.19 Hz, 1H), 2.93 (d, J=13.19 Hz, 1H), 2.59 (d, J=10.44 Hz, 1H), 2.41 (d, J=13.19 Hz, 1H), 2.23-2.11 (m, 1H), 1.68 (br. s., 1H), 1.52 (t, J=3.85 Hz, 1H), 1.46-1.31 (m, 2H), 1.27 (t, J=7.15 Hz, 3H), 1.10 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e41cd72f15a042a88ce20b5282e9f525
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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