4-Methylmorpholine → [3-(3,4-Dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidin-1-yl](2-methoxyphenyl)methanone

Temperature

0 °C

3-(3,4-Dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine, (218 mg, 0.83 mmol) was dissolved in dichloromethane at -78° C. and treated with 4-methylmorpholine (0.19 mL, 1.73 mmol, 2 eq.) and 2-methoxybenzoyl chloride (155 mg, 0.84 mmol, 1 eq.) in dichloromethane (3×1 mL). The solution was allowed to warm to 0° C. and stir for 4.5 hours. The solution was washed with 1N HCl and 5% sodium bicarbonate and the organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (30 g) with a gradient of 50% ethyl acetate in hexane to 6% methanol in dichloromethane to give 202 mg (60%) of the title compound.

1. washThe solution was washed with 1N HCl and 5% sodium bicarbonate
2. dry with materialthe organic phase was dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed on silica gel (30 g) with a gradient of 50% ethyl acetate in hexane to 6% methanol in dichloromethane

ORD record

ord-552f059a12ba47afbd1c516499ccffd1

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05635510