Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate → Methyl 2,4-dimethyl-3-pyrrolepropionate

Methyl 5-(benzyloxycarbonyl)-2,4-dimethyl-3-pyrrolepropionate (3.1 g, 9.8 mmol) was dissolved in acetone (100 mL). This solution was added with 10% Pd—C, and stirred at room temperature under hydrogen gas. When the starting material disappeared, the reaction mixture was filtered, and the filtrate was distilled under reduced pressure. The residue was added with trifluoroacetic acid (10 mL), and heated at 40° C. for 10 minutes under an argon flow. The reaction mixture was added with chloroform, and washed once with water, and the aqueous layer was extracted twice with chloroform. The organic phases were combined, washed once with aqueous Na2CO3 and once with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: CH2Cl2) to obtain the target compound as brown liquid (1.6 g, yield: 90%).

1. filtrationthe reaction mixture was filtered
2. distillationthe filtrate was distilled under reduced pressure
3. additionThe residue was added with trifluoroacetic acid (10 mL)
4. temperatureheated at 40° C. for 10 minutes under an argon flow
5. additionThe reaction mixture was added with chloroform
6. washwashed once with water
7. extractionthe aqueous layer was extracted twice with chloroform
8. washwashed once with aqueous Na2CO3 and once with water
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (developing solvent: CH2Cl2)

ORD record

ord-7d1069f2f2a14e0f88456f3c0d9c5ac8

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673957B2