Reaktion #41202

Reaktionsgleichung

Propargyl bromide

product

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

K2CO3

→

title compound

Ausbeute 88.5%

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

Ausbeute 88.5%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle