Reacción #41202

Ecuación de reacción

Propargyl bromide

product

2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

K2CO3

→

title compound

Rendimiento 88.5%

2-(4-Prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Rendimiento 88.5%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture stirred at 50° C. for 6 h
2. 2
   workup.WAITat rt for 48 h
3. 3
   ConcentraciónThe reaction mixture was concentrated
4. 4
   Lavadowashed with water
5. 5
   Secadodried over anhydrous MgSO4
6. 6
   Otrothe solvent removed in vacuo
7. 7
   OtroThe product was purified by silica gel flash chromatography

Procedimiento

To a solution of the product from step 2 (2.0 g, 6.82 mmol) in anhydrous DMF (50 mL) was added dry K2CO3 (4.6 g, 33 mmol) and allowed to stir for 15 min. Propargyl bromide (1.214 g, 10.20 mmol) in anhydrous DMF (10 mL) was added and the reaction mixture stirred at 50° C. for 6 h, then at rt for 48 h. The reaction mixture was concentrated, taken up in EtOAc, washed with water, dried over anhydrous MgSO4 and the solvent removed in vacuo. The product was purified by silica gel flash chromatography using EtOAc/hexane to obtain the title compound (2.0 g, 88%).

Fuente