2-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-isoindoline-1,3-dione → 1-(3-(1,3-dioxoisoindolin-2-yl)propyl)-1H-1,2,3-triazole-4-carbaldehyde

HRID 628687Notes

Reaction equation

HRID 628687 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[O:20]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]1[CH2:10][CH2:9][CH2:8][N:6]1[CH:7]=[C:3]([CH:2]=[O:1])[N:4]=[N:5]1

Participants

4

Reactant 1

HCID 591763832-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-isoindoline-1,3-dione

Product 1

HCID 591766301-(3-(1,3-dioxoisoindolin-2-yl)propyl)-1H-1,2,3-triazole-4-carbaldehydeYield 31.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the regioisomers 21 (0.77 g, 2.69 mmol) in dichloromethane (10 mL) was treated with manganese dioxide (0.94 g, 10.77 mmol). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through Celite and concentrated. The crude product was purified by silica gel chromatography (0-5% methanol/CH2Cl2) to afford 0.24 g (31% yield) of 22 as a single regioisomer: 1H NMR (400 MHz, CDCl3) δ 10.08 (s, 1H), 8.34 (s, 1H), 7.85-7.65 (m, 4H), 4.45 (t, J=12.0 Hz, 2H), 3.77-3.71 (m, 2H), 2.42-2.34 (m, 2H); ESI+ MS: m/z (rel intensity) 285.0 (100, [M+H]+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel chromatography (0-5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-d15d3712093c4de4bfb7c571e2c56a61
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

Loading…