HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 4-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | {4-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic Acid Tert-Butyl Ester | HCID 67006987 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Benzyloxy-1-[2-(4-methylaminomethyl-phenyl)-ethyl]-1H-pyridin-2-one | HCID 58042805 | — |
Reaction Steps
To 100 mg (0.22 mmol) {4-[2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-benzyl}-methyl-carbamic acid tert-butyl ester (example 19.1a) in DCM is added at RT 0.70 mL trifluoro-acetic acid. The reaction mixture is stirred 2 h at RT, neutralized with aqueous saturated NaHCO3-solution and is diluted with water and DCM. The layers are separated, the aqueous phase is extracted twice with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067590B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-fe6e93aa3a3344ee81f01348629ece05 |
| Source note | uspto-grants-2011_11 |