Hydrochloric Acid → HCID 18621453, compound

HRID 1861783Notes

Reaction equation

HRID 1861783 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCO.O=[Pt]=O>[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18621549HCID 18621549, compound

Product 1

HCID 18621453HCID 18621453, compoundYield 113.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of diethyl 2-((4-benzylpyridin-2-yl)methyl)malonate (2.6 g, 7.6 mmol) in EtOH (30 mL) were added PtO2 (70 mg) and conc. HCl (0.7 mL). The heterogeneous mixture was hydrogenated in a Parr hydrogenator at 30-35 psi at 25° C. for 16 h. The reaction was filtered through a Celite pad and was concentrated under reduced pressure to give the crude title compound as a yellow oil (3.0 g, 100%): 1H NMR (CDCl3) δ1.10-1.30 (m, 6H), 1.50-2.00 (m, 6H), 2.20-2.35 (m, 1H), 2.50-2.65 (m, 2H), 2.65-2.85 (m, 1H), 3.00-3.15 (m, 1H), 3.55-3.70 (m, JH), 3.90-4.05 (m, 1H), 4.05-4.30 (m, 4H), 7.08-7.32 (m, SH), 9.70 (bs, 2H) ; IR (film) 2927, 1735 cm−1.

Workup

  1. filtrationThe reaction was filtered through a Celite pad
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0c69d647ea04071b208c5be700fda26
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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