Réaction #89707

Équation de réaction

N,N-diisopropyl ethylamine

(2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid

BOP reagent

3-phenyl-pyrrolidine

→

crude product

Rendement 104.9%

tert-butyl(2S,3S)-5-(2-methoxy-2-oxoethyl)-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylate

Rendement 104.9%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreTo an oven-dried 5 mL conical vial equipped with a magnetic stir bar and under a nitrogen gas atmosphere
2. 2
   Autrethe reaction was quenched with 5% citric acid (1 mL)
3. 3
   workup.ADDITIONthe reaction mixture was diluted with ethyl acetate (15 mL) and water (4 mL)
4. 4
   ExtractionThe aqueous layer was extracted with ethyl acetate (3×3 mL)
5. 5
   Lavagethe combined organic phases were washed with saturated sodium bicarbonate (3×5 mL), brine (5 mL)
6. 6
   Séchagedried (NaSO4)
7. 7
   Concentrationconcentrated in-vacuo

Mode opératoire

To an oven-dried 5 mL conical vial equipped with a magnetic stir bar and under a nitrogen gas atmosphere was placed sequentially: (2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid (50 mg, 0.166 mmol), anhydrous DMF (2 mL), BOP reagent (100 mg, 0.226 mmol), 3-phenyl-pyrrolidine (25 mg, 0.17 mmol), and N,N-diisopropyl ethylamine (0.086 mL, 0.49 mmol). After stirring the reaction mixture overnight, the reaction was quenched with 5% citric acid (1 mL) and the reaction mixture was diluted with ethyl acetate (15 mL) and water (4 mL). The aqueous layer was extracted with ethyl acetate (3×3 mL) and the combined organic phases were washed with saturated sodium bicarbonate (3×5 mL), brine (5 mL), dried (NaSO4), and concentrated in-vacuo to afford 75 mg of crude product that was used directly in the following hydrolysis. LCMS (ESI): 431 (M+H), 375 (M-t-Bu+2H+).

Source