Triethylamine → Pyridine-2-carboxylic acid 4-(pyrrolidine-1-carbonyloxymethyl)-cyclohexyl ester

HRID 68484

Reaction equation

HRID 68484 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:4][CH2:3]1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](Cl)=[O:24].C(N(CC)CC)C>C(Cl)Cl.O>[N:12]1([C:10]([O:9][CH2:8][CH:5]2[CH2:6][CH2:7][CH:2]([O:1][C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)=[O:24])[CH2:3][CH2:4]2)=[O:11])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 66837799Pyrrolidine-1-carboxylic acid 4-hydroxycyclohexylmethyl ester

Product 1

HCID 56952073Pyridine-2-carboxylic acid 4-(pyrrolidine-1-carbonyloxymethyl)-cyclohexyl esterYield 70.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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).

Workup

  1. extractionfollowed by few times of extraction with methylene chloride
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-cbcbb27e30584e42ab30cd8da7dcaf04
Source dataset
uspto-grants-2014_09
Patent number
US08822463B2

Linked notes

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