Acetic Acid → Methyl 2-(cyclohexylmethyl)piperidine-4-carboxylate

HRID 1963126Notes

Reaction equation

HRID 1963126 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O=[Pt]=O.CO>[CH:2]1([CH2:1][CH:8]2[CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][NH:17]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66731507Methyl 2-benzylisonicotinate

Product 1

HCID 66732253Methyl 2-(cyclohexylmethyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-benzylisonicotinate (1.29 g, 5.67 mmol) and PtO2 (0.13 g, 0.57 mmol) were added to acetic acid (50 mL). The reaction mixture was hydrogenated in a Büchi hydrogentor at 8 bar at room temperature for 3 days. Methanol (100 mL) was added and the catalyst filtered off. The solvent was evaporated. The crude product was partitioned between Na2CO3 (aq) and ethyl acetate. The organic phase was isolated, dried over Na2SO4, filtered through Celite® and the solvent was evaporated. 1H NMR (600 MHz, cdcl3) δ 0.78-0.91 (m, 2H), 1.04-1.27 (m, 5H), 1.27-1.38 (m, 1H), 1.48 (ddd, 2H), 1.63 (dd, 5H), 1.80-1.93 (m, 2H), 2.36 (tt, 1H), 2.51-2.57 (m, 1H), 2.61 (td, 1H), 3.11 (ddd, 1H), 3.64 (s, 3H).

Workup

  1. filtrationthe catalyst filtered off
  2. customThe solvent was evaporated
  3. customThe crude product was partitioned between Na2CO3 (aq) and ethyl acetate
  4. customThe organic phase was isolated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through Celite®
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-910e45210ed14d42aad2d91cd86402ef
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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