3-Pyridineacetic acid → 3-Piperidineacetic acid

HRID 525491Notes

Reaction equation

HRID 525491 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=[O:9])[CH:2]=1>CC(O)=O.O=[Pt]=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][C:8]([OH:10])=[O:9])[CH2:2]1

Participants

4

Reactant 1

HCID 1083-Pyridineacetic acid

Product 1

HCID 2836963-Piperidineacetic acid

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(pyridin-3-yl)acetic acid (274 mg, 2.0 mmol, 1.0 eq) in AcOH (2 mL) was added PtO2 (226 mg, 1.0 mmol, 0.5 eq). The mixture was stirred at room temperature for 16 h under H2. The catalyst was filtered out and the filtrate was concentrated to give 2-(piperidin-3-yl)acetic acid as a slight yellow solid (300 mg, Y: 81%). ESI-MS (M+H)+: 143.1. 1H NMR (400 MHz, CD3OD) δ: 3.34-3.31 (m, 1H), 2.84-2.77 (m, 1H), 2.64-2.57 (m, 3H), 2.18-2.10 (m, 3H), 1.86-1.83 (m, 2H), 1.71-1.67 (m, 1H), 1.24-1.22 (m, 1H).

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-df610b6746b342d8a0d39e7e728fed9e
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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