Reaktion #1942841

Reaktionsgleichung

ammonia

N-(3-butynyl)phthalimide

2,2-dimethylpropionic acid azidomethyl ester

sodium ascorbate

→

2,2-dimethylpropionic acid 4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,3]triazol-1-ylmethyl ester

Ausbeute 88.7%

Lösungsmittel

water t-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction medium is extracted with EtOAc
2. 2
   WaschenThe organic phase is then washed with brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated

Vorschrift

702 mg (3.52 mmol) of N-(3-butynyl)phthalimide and 552 mg (3.51 mmol) of 2,2-dimethylpropionic acid azidomethyl ester are suspended in a water/t-butanol mixture (1/1, 10.5 ml). 0.18 ml of a 1M CuSO4 solution is added. 206 mg (1.04 mmol) of sodium ascorbate are then added. After 4 hours, the reaction is stopped by adding aqueous ammonia solution, and the reaction medium is extracted with EtOAc. The organic phase is then washed with brine and dried over MgSO4, filtered and concentrated. 1.11 g of 2,2-dimethylpropionic acid 4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,3]triazol-1-ylmethyl ester in the form of a yellow oil are obtained in a yield of 88%.

Quelle