p-Toluenesulfonic acid → 1-[1-(1H-1,2,4-triazol-1-ylmethyl) tricyclo[3.3.1.03,7]non-3-yl]ethanone

HRID 1015531Notes

Reaction equation

HRID 1015531 reaction equation
[CH3:1][C:2]1([C:7]23[CH2:14][CH:13]4[CH2:15][C:9]([CH2:16][N:17]5[CH:21]=[N:20][CH:19]=[N:18]5)([CH2:10][CH:11]2[CH2:12]4)[CH2:8]3)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[N:17]1([CH2:16][C:9]23[CH2:15][CH:13]4[CH2:12][CH:11]([CH2:10]2)[C:7]([C:2](=[O:3])[CH3:1])([CH2:14]4)[CH2:8]3)[CH:21]=[N:20][CH:19]=[N:18]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 673004551-{[3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo [3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole

Product 1

HCID 670178781-[1-(1H-1,2,4-triazol-1-ylmethyl) tricyclo[3.3.1.03,7]non-3-yl]ethanoneYield 98.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 1-{[3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methyl}-1H-1,2,4-triazole (2.6 g, 9.09 mmol) obtained from Step I and p-toluenesulfonic acid (0.16 g) in acetone (36 mL) was refluxed for 4 h. The volatiles were removed under reduced pressure and the residue was diluted with ethylacetate, washed with 10% aq. NaHCO3 and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-[1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (2.2 g, 86% yield) as a viscous liquid. m/z (M+1) 246; 1H NMR (CDCl3) 300 MHz δ 7.99 (s, 1H), 7.93 (s, 1H), 4.10 (s, 2H), 2.75-2.65 (m, 1H), 2.49-2.42 (m, 1H), 2.16 (s, 3H), 2.0-1.45 (m, 10H). 13C NMR (CDCl3) 75 MHz δ 211.0, 151.6, 143.6, 61.6, 56.9, 48.2, 45.9, 45.7, 42.6, 41.9, 37.3, 36.6, 26.3.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was diluted with ethylacetate
  3. washwashed with 10% aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-28437c80e6a74a03906428c63ac21f98
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

Loading…