Sulfur → HCID 11736779, compound

HRID 254839Notes

Reaction equation

HRID 254839 reaction equation
[C:1]([O:5][CH2:6][CH:7]1[CH:12]=[CH:11][N:10](C(=O)C(C)(C)C)[CH:9]=[C:8]1[CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])([CH3:4])([CH3:3])[CH3:2].[S]>C1(C)C=CC=CC=1>[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 11336591HCID 11336591, compound

Product 1

HCID 11736779HCID 11736779, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-[4-tert-butoxymethyl-3-(1-methylpyrrolidin-2-yl)-4H-pyridin-1-yl]-2,2-dimethyl-propan-1-one (0.194 g, 0.5 mmol), sulfur (0.02 g, 0.5 mmol) and toluene (5 mL) was refluxed for 1 day. 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 0.091 g (54%) of 4-tert-butoxymethyl-3-(1-methylpyrrolidin-2-yl)-pyridine as a yellow oil. IR (thin film, neat, NaCl) 2970, 2778, 1594, 1362, 1193, 1088 cm−1; 1H NMR (CDCl3, 400 MHz) δ 8.72 (s, 1H), 8.45 (d, 1H, J=6.4 Hz), 7.40 (d, 1H, J=6.4 Hz), 4.52 (s, 2H), 3.32-3.20 (m, 3H), 2.32-2.22 (m, 2H), 2.18 (s, 3H), 1.96-1.66 (m, 4H), 1.29 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 148.3, 147.7, 146.2, 135.3, 121.4, 73.4, 65.2, 59.6, 56.5, 40.2, 33.7, 27.20, 22.4; HRMS Calcd for C15H24N2O: 249.1967 [M+H]+. Found: 249.1964 [M+H]+. [α]D28−108.2 (c 3.4, 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-d0570f2a7e5b47e0b7168044c9788792
Source dataset
uspto-grants-2011_01
Patent number
US07875724B2

Reaction notes

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