Sulfur → 5-(1-Methylpyrrolidin-2-yl)pyridine-3-carbaldehyde

HRID 719749Notes

Reaction equation

HRID 719749 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH2:8][C:9]([CH:13]=[O:14])=[CH:10][NH:11][CH:12]=1.[S]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:8]=[C:9]([CH:13]=[O:14])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 58594484HCID 58594484, compound

Product 1

HCID 219018805-(1-Methylpyrrolidin-2-yl)pyridine-3-carbaldehydeYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (S)-5-(1-methylpyrrolidin-2-yl)-1,4-dihydropyridine-3-carbaldehyde IV (0.011 g, 0.044 mmol) and elemental sulfur (0.0015 g, 0.044 mmol) in 2 mL of toluene was refluxed for 1 day. After filtration through a pad of Celite, and evaporation of the solvent under reduced pressure, the crude material was purified by RPLC (silica gel, 5% EtOAc/hexanes then EtOAc) to afford 0.007 g (83%) of 5-(1-methylpyrrolidin-2-yl)pyridine-3-carbaldehyde V as a clear oil. IR (thin film, neat, NaCl): 2950, 1586, 1370, 1120 cm−1. 1H NMR (CDCl3, 300 MHz) δ 10.13–10.12 (m, 1 H), 8.97–8.96 (m, 1 H), 8.79 (s, 1 H), 8.18 (s, 1 H), 3.30–3.20 (m, 2 H), 2.38–1.67 (m, 4 H); 13C NMR (CDCl3, 100 MHz) δ 191.26, 154.81, 150.91, 135.13, 131.69, 68.53, 57.19, 40.64, 40.64, 35.66, 23.02. HRMS Calcd for C11H14N2O: 191.1184 [M+H]+. Found: 191.1182 [M+H]+. [α]23D−92 (c=0.2, CH2Cl2).

Workup

  1. filtrationAfter filtration
  2. customthrough a pad of Celite, and evaporation of the solvent under reduced pressure
  3. customthe crude material was purified by RPLC (silica gel, 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-9172ac50b1064f0b882c1915c7ebb6ca
Source dataset
uspto-grants-2006_11
Patent number
US07132545B2

Reaction notes

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