Sulfur → 4-Benzyloxymethyl-3-(1-methylpyrrolidin-2-yl)-pyridine

HRID 968911Notes

Reaction equation

HRID 968911 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH:15]=[CH:14][N:13](C(=O)C(C)(C)C)[CH:12]=[C:11]1[CH:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S]>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[CH:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 219460401-[4-benzyloxymethyl-3-(1-methylpyrrolidin-2-yl)-4H-pyridin-1-yl]-2,2-dimethyl-propan-1-one

Product 1

HCID 219460434-Benzyloxymethyl-3-(1-methylpyrrolidin-2-yl)-pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-[4-benzyloxymethyl-3-(1-methylpyrrolidin-2-yl)-4H-pyridin-1-yl]-2,2-dimethyl-propan-1-one (0.176 g, 0.48 mmol), sulfur (0.015 g. 0.48 mmol) and toluene (5 mL) was refluxed for 3 days. After filtration of the mixture through a pad of Celite and evaporation of the solvent under reduced pressure, the crude material was purified by radial PLC (hexanes) to afford 0.08 g (60%) of 4-benzyloxymethyl-3-(1-methylpyrrolidin-2-yl) -pyridine as a yellow oil. IR (thin film, neat, NaCl) 3436, 1637, 1090 cm−1; 1H NMR (CDCl3, 300 MHz) δ 8.74 (s, 1 H), 8.47 (d, 1 H, J=4.8 Hz), 7.40-7.27 (m, 6 H), 4.62 (d, 2 H,J=13. 2 Hz), 3.34-3.18 (m, 2 H), 2.28-2.18 (m, 2 H), 2.15 (s, 3 H), 2.11-1.09 (m, 5 H); 13C NMR (CDCl3, 75 MHz) δ 149.31, 148.37, 145.16, 137.86, 128.67, 128.06, 127.98, 122.14, 72.92, 68.19, 65.88, 57.07, 40.75, 34.28, 27.83, 22.91; HRMS Calcd for C18H22N2O: 283.1810 [M+H]+. Found: 283.1800 [M+H]+. [α]D24−75.9 (c 2.5, CH2Cl2).

Workup

  1. filtrationAfter filtration of the mixture
  2. customthrough a pad of Celite and evaporation of the solvent under reduced pressure
  3. customthe crude material was purified by radial PLC (hexanes)

Sources & evidence

ORD record
ord-656f3c0c1565425da767d7a819bf32ef
Source dataset
uspto-grants-2007_12
Patent number
US07304160B2

Reaction notes

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