反应详情

To a stirred solution of 2-butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.753 g, 2.95 mmol) in THF (12 mL) at 0° C. and under nitrogen was added 3,4-dichlorophenylmagnesium bromide (11.8 mL of a 0.5 M solution in pentanes, 5.9 mmol) dropwise over 10 minutes. After 20 minutes, the reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL) then extracted with EtOAc. The combined extracts were washed with brine then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (1.9 g). Purification by chromatography (silica, 5-20% EtOAc in hexanes) gave 2-butyl-2-[(3,4-dichloro-phenyl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.548 g, 1.36 mmol, 46%) as a colourless gum and as an inseparable mixture of diastereomers

1. customthe reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL)
2. extractionthen extracted with EtOAc
3. washThe combined extracts were washed with brine
4. dry with materialthen dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo to a yellow oil (1.9 g)
7. customPurification by chromatography (silica, 5-20% EtOAc in hexanes)