Sodium Bicarbonate → (R)-1-[1-(4-Chloro-phenyl)-cyclobutanecarbonyl]-piperidine-3-carboxylic acid ethyl ester

Ethyl (R)-nipecotate L-tartrate (15.0 g, 48.8 mmol) was added to a stirred mixture of dichloromethane and saturated sodium bicarbonate solution (100 mL each) at 0° C. After 10 min 1-(4-chloro-phenyl)-cyclobutanecarbonyl chloride (11.13 g, 48.8 mmol) was slowly added at 0° C. The reaction was then allowed to stir for 2 h at room temperature. The organic layer was separated and the aqueous layer was washed once with dichloromethane (100 mL). The organic material was combined and washed once with water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (2:1) to give 9.2 g of the amidester as a thick clear gum; C19H24ClNO3, LRMS (m/z)=350 (MH+).

1. customThe organic layer was separated
2. washthe aqueous layer was washed once with dichloromethane (100 mL)
3. washwashed once with water (100 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation
7. customThe residue was purified by chromatography on silica gel
8. washeluting with hexane/ethyl acetate (2:1)
9. customto give 9.2 g of the amidester as a thick clear gum

ORD record

ord-5bb909e8b0254c3ab18e426557a4d294

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517892B2