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

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%).

1. stirringthe reaction mixture stirred at 50° C. for 6 h
2. waitat rt for 48 h
3. concentrationThe reaction mixture was concentrated
4. washwashed with water
5. dry with materialdried over anhydrous MgSO4
6. customthe solvent removed in vacuo
7. customThe product was purified by silica gel flash chromatography

ORD record

ord-c118b8ac54d14d2ab9d48661c465d8e7

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728032B2