Reaction #155666

Reaction equation

pyrrolidine-1-carboxylic acid 4-hydroxy-cyclohexylmethyl ester

picolinoyl chloride

triethylamine

→

compound

Yield 70.1%

pyridine-2-carboxylic acid 4-(pyrrolidine-1-carbonyloxymethyl)-cyclohexyl ester

Yield 70.1%

Solvents

methylene chloride

water

Conditions

Workup

1. 1
   Extractionfollowed by few times of extraction with methylene chloride
2. 2
   DryingThe combined organic layer was dried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified by column chromatography (silica gel, ethyl acetate)

Procedure

To a solution of pyrrolidine-1-carboxylic acid 4-hydroxy-cyclohexylmethyl ester (1 mmol) in methylene chloride (5 mL) were added picolinoyl chloride (1.1 mmol) and triethylamine (1.5 mmol) and the resulting mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with water, followed by few times of extraction with methylene chloride. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, ethyl acetate), thereby completing the preparation of a target compound (233 mg, 70% yield).

Source