2-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dione → 2-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-isoindoline-1,3-dione

HRID 628686Notes

Reaction equation

HRID 628686 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])=[N+:2]=[N-:3]>C(O)C#C>[OH:16][CH2:15][C:14]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH:13]=1

Participants

3

Reactant 1

HCID 1864562-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

A solution of 2-(3-azidopropyl)isoindoline-1,3-dione, 20, (0.62 g, 2.69 mmol) in propargyl alcohol (4 mL) was warmed to 90° C. and stirred for 18 h. The reaction mixture was concentrated under reduced pressure. The crude product containing both regioisomers (˜1:1 ratio) was used in the next step without further purification. ESI+ MS: m/z (rel intensity) 301.1 (100, [M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe crude product containing both regioisomers (˜1:1 ratio)
  3. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-1ce005dbca5547e492196c05a39e021d
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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