HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate | HCID 854071 | — |
| Reactant | 2-(4-Chloroquinolin-2-yl)phenol | HCID 135547052 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | (S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylate | HCID 136068479 | 42.3% |
Reaction Steps
A solution of (S)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (0.218 g, 1.173 mmol) and 2-(4-chloroquinolin-2-yl)phenol (0.100 g, 0.391 mmol) in DMSO (2 mL) was heated under microwave conditions at 155° C. for 1.5 hours. The mixture was added to water (50 mL) and extracted with diethyl ether (2×20 mL). The organic layers were combined, dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (30-40% ethyl acetate/hexane) to give the title compound (0.067 g, 42%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324226B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-1f3f72d14b0242ebbd07d0804180dc75 |
| Source note | uspto-grants-2012_12 |